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tacrolimus
ethanone, 1-(2,4,4,5,5-pentamethyl-1-cyclopenten-1-yl)-

Supplier Sponsors

Name:1-(2,4,4,5,5-pentamethylcyclopenten-1-yl)ethanone
CAS Number: 13144-88-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:236-080-0
Nikkaji Web:J317.831E
XlogP3-AA:2.80 (est)
Molecular Weight:180.29060000
Formula:C12 H20 O
NMR Predictor:Predict (works with chrome or firefox)
Category:fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Patents:Search
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Pubchem Patents:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 232.00 to 233.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.058000 mmHg @ 25.00 °C. (est)
Flash Point: 188.00 °F. TCC ( 86.70 °C. ) (est)
logP (o/w): 3.369 (est)
Soluble in:
 alcohol
 water, 19.61 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
1-(2,4,4,5,5-Pentamethyl-1-cyclopenten-1-yl)ethan-1-one
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: fragrance agents
IFRA Critical Effect: Sensitization
IFRA: View Standard
Fragrance usage is IFRA RESTRICTED. View Standard for complete information.
Please review all IFRA documents for complete information.
IFRA categories: limits in the finished product: (For a description of the categories, refer to the IFRA QRA Information Booklet.)
Category 1:
See Note (1)
0.03 % (1)
Category 2:  0.04 %
Category 3:  0.15 %
Category 4:  0.45 %
Category 5:  0.24 %
Category 6:
See Note (1)
0.72 % (1)
Category 7:  0.08 %
Category 8:  1.01 %
Category 9:  5.00 %
Category 10:  2.50 %
Category 11: See Note (2)
 Notes:
 

(1) IFRA would recommend that any material used to impart perfume or flavour in products intended for human ingestion should consist of ingredients that are in compliance with appropriate regulations for foods and food flavourings in the countries of planned distribution and, where these are lacking, with the recommendations laid down in the Code of Practice of IOFI (International Organisation of the Flavor Industry). Further information about IOFI can be found on its website (www.iofi.org).

 

(2) Category 11 includes all non-skin contact or incidental skin contact products. Due to the negligible skin contact from these types of products there is no justification for a restriction of the concentration of this fragrance ingredient in the finished product.

 
Recommendation for tacrolimus flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
EPA Substance Registry Services (TSCA):13144-88-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :83177
National Institute of Allergy and Infectious Diseases:Data
1-(2,4,4,5,5-pentamethylcyclopenten-1-yl)ethanone
Chemidplus:0013144882
 
References:
 1-(2,4,4,5,5-pentamethylcyclopenten-1-yl)ethanone
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:13144-88-2
Pubchem (cid):83177
Pubchem (sid):135040422
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
2-acetyl-1,3,3,4,4-pentamethyl cyclopentene
2-acetyl-1,3,3,4,4-pentamethylcyclopentene
 ethanone, 1-(2,4,4,5,5-pentamethyl-1-cyclopenten-1-yl)-
 pentamethyl cyclopent-1-enyl methyl ketone
1-(2,4,4,5,5-pentamethyl-1-cyclopenten-1-yl) ethan-1-one
1-(2,4,4,5,5-pentamethyl-1-cyclopenten-1-yl)ethan-1-one
1-(2,4,4,5,5-pentamethylcyclopent-1-en-1-yl)ethanone
1-(2,4,4,5,5-pentamethylcyclopenten-1-yl)ethanone
 tacrolimus
 

Articles:

PubMed:Reduced variability of tacrolimus trough level in once-daily tacrolimus-based Taiwanese kidney transplant recipients with high-expressive genotype of cytochrome P450 3A5.
PubMed:Chemometric Methods for the Quantification of Crystalline Tacrolimus in Solid Dispersion by Powder X-Ray Diffractrometry.
PubMed:Management of difficult-to-treat atopic dermatitis.
PubMed:Effect of Tacrolimus on the pharmacokinetics of bioactive lignans of Wuzhi tablet (Schisandra sphenanthera extract) and the potential roles of CYP3A and P-gp.
PubMed:Determination of bioequivalence for drugs with narrow therapeutic index: reduction of the regulatory burden.
PubMed:KM110329 in adult patients with atopic dermatitis: a randomised, double-blind, placebo-controlled, multicentre trial--study protocol.
PubMed:New developments in transplant-acquired allergies.
PubMed:Addition of mycophenolate mofetil to tacrolimus is associated with decreases in food-specific IgE levels in a pediatric patient with liver transplantation-associated food allergy.
PubMed:Off-label topical calcineurin inhibitor use in children.
PubMed:Impact of CYP3A5 genetic polymorphisms on the pharmacokinetics and short-term remission in patients with ulcerative colitis treated with tacrolimus.
PubMed:Clinical, endoscopic, and histologic features of eosinophilic inflammation of the gastrointestinal tract in pediatric liver transplant patients.
PubMed:Analyses of marketplace tacrolimus drug product quality: bioactivity, NMR and LC-MS.
PubMed:Atopic dermatitis induced by systemic immunosupression with tacrolimus--case report.
PubMed:From gut to kidney: transporting and metabolizing calcineurin-inhibitors in solid organ transplantation.
PubMed:Topical calcineurin inhibitors and lymphoma risk: evidence update with implications for daily practice.
PubMed:Molecular cloning and characterization of two 12 kDa FK506-binding protein genes in the Chinese oak silkworm, Antheraea pernyi.
PubMed:Food, food components, and botanicals affecting drug metabolism in transplantation.
PubMed:Post-transplant food allergy in children is associated with liver and not with renal transplantation: a monocentric comparative study.
PubMed:[Four new drugs on the market: abiraterone, belatacept, vandetanib and fidaxomycine].
PubMed:Protein phosphatase-dependent circadian regulation of intermediate-term associative memory.
PubMed:Methods, strengths, weaknesses, and limitations of bioequivalence tests with special regard to immunosuppressive drugs.
PubMed:Long-term follow-up of de novo allergy in pediatric liver transplantation--10 yr experience of a single center.
PubMed:Pomegranate-containing products and tacrolimus: a potential interaction.
PubMed:Therapeutic drug monitoring of posaconazole in patients with acute myeloid leukemia or myelodysplastic syndrome.
PubMed:Atopic dermatitis: an overview.
PubMed:Signals of progressive multifocal leukoencephalopathy for immunosuppressants: a disproportionality analysis of spontaneous reports within the US Adverse Event Reporting System (AERS).
PubMed:Guidelines for treatment of atopic eczema (atopic dermatitis) Part II.
PubMed:Guidelines for treatment of atopic eczema (atopic dermatitis) part I.
PubMed:Association of hepatitis B with antirheumatic drugs: a case-control study.
PubMed:A randomized pharmacokinetic study of generic tacrolimus versus reference tacrolimus in kidney transplant recipients.
PubMed:Food allergy after cord blood stem cell transplantation with tacrolimus therapy in two patients who developed veno-occlusive disease.
PubMed:De novo food sensitization and eosinophilic gastrointestinal disease in children post-liver transplantation.
PubMed:Effect of clinical condition and mycophenolate mofetil on plasma retinol, α-tocopherol and β-carotene in renal transplant recipients.
PubMed:Post-transplantation encapsulating peritoneal sclerosis in a pediatric patient.
PubMed:Calcineurin inhibitor minimisation versus continuation of calcineurin inhibitor treatment for liver transplant recipients.
PubMed:Anti-diabetic and anti-obesity agent sodium tungstate enhances GCN pathway activation through Glc7p inhibition.
PubMed:Belatacept: a new biologic and its role in kidney transplantation.
PubMed:Clinical and immunological changes of immunotherapy in patients with atopic dermatitis: randomized controlled trial.
PubMed:Food-drug interaction of tacrolimus with pomelo, ginger, and turmeric juice in rats.
PubMed:Crystallinity evaluation of tacrolimus solid dispersions by chemometric analysis.
PubMed:Generic maintenance immunosuppression in solid organ transplant recipients.
PubMed:Citrus grandis peel increases the bioavailability of cyclosporine and tacrolimus, two important immunosuppressants, in rats.
PubMed:[Treatment-resistant adult atopic dermatitis].
PubMed:A multicenter experience with generic tacrolimus conversion.
PubMed:What's new in atopic eczema? An analysis of systematic reviews published in 2009-2010.
PubMed:Eczema.
PubMed:Expression and regulation of the Fkbp5 gene in the adult mouse brain.
PubMed:Management of post-liver transplant-associated IgE-mediated food allergy in children.
PubMed:The "generic" effect of food on tacrolimus pharmacokinetics.
PubMed:[Septic shock in a renal transplanted patient after consumption of uncooked pork meat].
PubMed:Pipecolic acid derivatives as small-molecule inhibitors of the Legionella MIP protein.
PubMed:The ryanodine receptor in cardiac physiology and disease.
PubMed:Management of drug and food interactions with azole antifungal agents in transplant recipients.
PubMed:Treatment of canine atopic dermatitis: 2010 clinical practice guidelines from the International Task Force on Canine Atopic Dermatitis.
PubMed:[Atopic dermatitis - current insights into path physiology and management].
PubMed:Bioequivalence testing of immunosuppressants: concepts and misconceptions.
PubMed:Long-standing oral mucosal lesions in solid organ-transplanted children-a novel clinical entity.
PubMed:[What's new in pediatric dermatology?].
PubMed:Understanding the genetic basis for adverse drug effects: the calcineurin inhibitors.
PubMed:Association between exposure to topical tacrolimus or pimecrolimus and cancers.
PubMed:Long-term glomerular filtration rate in liver allograft recipients according to the type of calcineurin inhibitors.
PubMed:Effects of orally administered Actinidia arguta (Hardy Kiwi) fruit extract on 2-chloro-1,3,5-trinitrobenzene-induced atopic dermatitis-like skin lesions in NC/Nga mice.
PubMed:ETFAD/EADV eczema task force 2009 position paper on diagnosis and treatment of atopic dermatitis.
PubMed:[Pediatric liver transplantation].
PubMed:Early outcomes of thymoglobulin and basiliximab induction in kidney transplantation: application of statistical approaches to reduce bias in observational comparisons.
PubMed:[Embryo development in rats treated with tacrolimus during the preimplantation phase].
PubMed:Tacrolimus levels in adult patients with renal transplant.
PubMed:[Use of Sirolimus in five pediatric patients undergoing solid organ transplantation].
PubMed:Cylex ImmuKnow assay levels are lower in lung transplant recipients with infection.
PubMed:Volatile organic nitrogen-containing constituents in ambrette seed Abelmoschus moschatus Medik (Malvaceae).
PubMed:Therapeutic management of posttransplant diabetes mellitus.
PubMed:Bioequivalence studies of tacrolimus capsule under fasting and fed conditions in healthy male and female subjects.
PubMed:Failure of immunosuppressive drug levels to predict T-cell reactivity in pediatric transplant patients.
PubMed:Synergistic effect of green tea polyphenols on their protection against FK506-induced cytotoxicity in renal cells.
PubMed:Modulation of cytokine production by plant sterols in stimulated human Jurkat T cells.
PubMed:A new pharmacologic action of CCI-779 involves FKBP12-independent inhibition of mTOR kinase activity and profound repression of global protein synthesis.
PubMed:Efficacy of tacrolimus in inhibiting inflammation caused by carrageenan in a murine model of air pouch.
PubMed:The AJT report.
PubMed:The US FDA 'black box' warning for topical calcineurin inhibitors: an ongoing controversy.
PubMed:New-onset post-transplantation food allergy in children--is it attributable only to the immunosuppressive protocol?
PubMed:Calcineurin primes immature gonadotropin-releasing hormone-secreting neuroendocrine cells for migration.
PubMed:An FKBP destabilization domain modulates protein levels in Plasmodium falciparum.
PubMed:[Influence of tacrolimus and ciprofloxacin on glucose metabolism].
PubMed:Orally administered lactoperoxidase increases expression of the FK506 binding protein 5 gene in epithelial cells of the small intestine of mice: a DNA microarray study.
PubMed:Tacrolimus (FK506) reduces hippocampal damage but fails to prevent learning and memory deficits after transient, global cerebral ischemia in rats.
PubMed:[Summary of the practice guideline 'Atopic dermatitis' (first revision) from the Dutch College of General Practitioners].
PubMed:[The practice guideline 'Atopic dermatitis' (first revision) from the Dutch College of General Practitioners: a response from the perspective of general practice].
PubMed:The development of eosinophilic colitis after liver transplantation in children.
PubMed:Safety of topical calcineurin inhibitors for the treatment of atopic dermatitis.
PubMed:Purification and characterization of an antifungal protein, C-FKBP, from Chinese cabbage.
PubMed:Tacrolimus severe overdosage after intake of masked grapefruit in orange marmalade.
PubMed:Topical calcineurin inhibitors revisited.
PubMed:Calcineurin inhibitors and rapamycin: cancer protection or promotion?
PubMed:Oral graft vs. host disease in children--treatment with topical tacrolimus ointment.
PubMed:Angioedema in renal transplant recipients on sirolimus.
PubMed:Submerged cultivation of Streptomyces tsukubaensis in media composed of waste products of food industry.
PubMed:clinical research, innovative practice and IRB review: identifying and respecting boundaries.
PubMed:Calcineurin inhibitors in the treatment of allergic dermatitis.
PubMed:Black box warning for topical calcineurin inhibitors and the death of common sense.
PubMed:Ginkgo biloba leaf extract (EGb761) combined with neuroprotective agents reduces the infarct volumes of gerbil ischemic brain.
PubMed:Topical calcineurin inhibitors labeling: putting the "box" in perspective.
PubMed:Tacrolimus-associated eosinophilic gastroenterocolitis in pediatric liver transplant recipients: role of potential food allergies in pathogenesis.
PubMed:Tacrolimus immunosuppression - an association with asymptomatic eosinophilia and elevated total and specific IgE levels.
PubMed:Food allergy after liver transplantation - is it the result of T-cell imbalance?
PubMed:Safety of topical calcineurin inhibitors in atopic dermatitis: evaluation of the evidence.
PubMed:Calcineurin is required for sclerotial development and pathogenicity of Sclerotinia sclerotiorum in an oxalic acid-independent manner.
PubMed:Polyomavirus-associated nephropathy: update of clinical management in kidney transplant patients.
PubMed:Food protein sensitivity with partial villous atrophy after pediatric liver transplantation with tacrolimus immunosuppression.
PubMed:Delayed effect of grapefruit juice on pharmacokinetics and pharmacodynamics of tacrolimus in a living-donor liver transplant recipient.
PubMed:Development of multiple food allergies in children taking tacrolimus after heart and liver transplantation.
PubMed:The use of topical calcineurin inhibitors in dermatology: safety concerns. Report of the American Academy of Dermatology Association Task Force.
PubMed:Protective effect of green tea extract and tea polyphenols against FK506-induced cytotoxicity in renal cells.
PubMed:Safety of St. John's Wort extract compared to synthetic antidepressants.
PubMed:The carcinogenic potential of tacrolimus ointment beyond immune suppression: a hypothesis creating case report.
PubMed:Extracorporeal photopheresis for acute and chronic graft-versus-host disease: does it work?
PubMed:Treatment of protein contact dermatitis with topical tacrolimus.
PubMed:The "black box" warning and allergy drugs.
PubMed:Severe angioedema caused by banana allergy under tacrolimus immunosuppression.
PubMed:Therapy of atopic eczema.
PubMed:A comparison of the effects of psychotomimetics and anxiolytics on punished and unpunished responding maintained by fixed interval schedules of food reinforcement in the rat.
PubMed:[Can the precautionary principle obstruct therapeutic progress?].
PubMed:Alcohol-induced rash caused by topical tacrolimus.
PubMed:Topical treatment tacrolimus and food allergy.
PubMed:[Current aspects of the therapy with topical calcineurin inhibitors].
PubMed:Consensus statement on the safety profile of topical calcineurin inhibitors.
PubMed:Effective therapy of childhood atopic dermatitis allays food allergy concerns.
PubMed:Tacrolimus in liver transplantation.
PubMed:Pimecrolimus and tacrolimus: the US FDA public health advisory.
PubMed:Fat apoptosis through targeted activation of caspase 8: a new mouse model of inducible and reversible lipoatrophy.
PubMed:Different evolution of trough and dose levels during the first year after transplantation for tacrolimus versus cyclosporine.
PubMed:The new therapeutic dilemma in pediatrics.
PubMed:[Viewpoint of the German Dermatologic Society (DDG) concerning the decision of the American Food and Drug Administration (FDA) on the use of pimecrolimus cream and tacrolimus ointment in the treatment of atopic dermatitis (neurodermatitis)].
PubMed:Position paper on diagnosis and treatment of atopic dermatitis.
PubMed:Transcriptional response of Saccharomyces cerevisiae to the plasma membrane-perturbing compound chitosan.
PubMed:[Treatment of atopic dermatitis: practical approach].
PubMed:Immunosuppression: evolution in practice and trends, 1993-2003.
PubMed:Exposure-response relationships and drug interactions of sirolimus.
PubMed:The development of food allergy after liver transplantation.
PubMed:Adult food allergy.
PubMed:[Tacrolimus hydrate (tacrolimus)].
PubMed:Tacrolimus ointment: utilization patterns in children under age 2 years.
PubMed:Clinical pharmacokinetics and pharmacodynamics of tacrolimus in solid organ transplantation.
PubMed:Newer Therapies for Inflammatory Bowel Disease.
PubMed:[Successful treatment by tacrolimus in two patients with Osserman's grade III intractable myasthenia gravis and elderly IIb].
PubMed:Synergistic efficacy of magnesium sulfate and FK506 on cerebral ischemia-induced infarct volume in gerbil.
PubMed:Effect of tacrolimus (FK506) on ischemia-induced brain damage and memory dysfunction in rats.
PubMed:Topical pimecrolimus in the treatment of human allergic contact dermatitis.
PubMed:Allergic disease after pediatric liver transplantation with systemic tacrolimus and cyclosporine a therapy.
PubMed:Tacrolimus and food allergy.
PubMed:Pharmacokinetics of pimecrolimus, a novel nonsteroid anti-inflammatory drug, after single and multiple oral administration.
PubMed:Systemic FK506 and post transplant food allergy in children.
PubMed:Influence of food on plasma concentration of mycophenolic acid in a heart transplant patient receiving concomitant tacrolimus.
PubMed:Outcomes in kidney transplantation.
PubMed:Immune cell function testing: an adjunct to therapeutic drug monitoring in transplant patient management.
PubMed:Angioedema in pediatric liver transplant recipients under tacrolimus immunosuppression.
PubMed:Topical tacrolimus Protopic.
PubMed:Sirolimus: new preparation. No tangible advance in renal transplantation.
PubMed:Atopic dermatitis: review of immunopathogenesis and advances in immunosuppressive therapy.
PubMed:Mechanisms of clinically relevant drug interactions associated with tacrolimus.
PubMed:Improved efficacy of basiliximab over antilymphocyte globulin induction therapy in paediatric renal transplantation.
PubMed:Food-drug interactions.
PubMed:The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?
PubMed:Tacrolimus ointment for the treatment of atopic dermatitis.
PubMed:Effective oral administration of tacrolimus in renal transplant recipients.
PubMed:Treatment of psoriasis. Part 2. Systemic therapies.
PubMed:Food allergy after pediatric organ transplantation with tacrolimus immunosuppression.
PubMed:Significant absorption of topical tacrolimus in 3 patients with Netherton syndrome.
PubMed:A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.
PubMed:Tacrolimus ointment for the treatment of steroid-induced rosacea: a preliminary report.
PubMed:US FDA advisory committee recommends approval of tacrolimus ointment.
PubMed:Clinical aspects of small-bowel transplantation.
PubMed:Pharmacological surrogates of allograft outcome.
PubMed:Effect of low- and high-fat meals on tacrolimus absorption following 5 mg single oral doses to healthy human subjects.
PubMed:From the Food and Drug Administration.
PubMed:Drug-grapefruit juice interactions.
PubMed:Nutritional immunomodulation leads to enhanced allograft survival in combination with cyclosporine A and rapamycin, but not FK506.
PubMed:Small bowel transplants in adults and multivisceral transplants in adults and children.
PubMed:Cumulative experience with pediatric living related liver transplantation.
PubMed:Overview of transplantation immunology and the pharmacotherapy of adult solid organ transplant recipients: focus on immunosuppression.
PubMed:Intestinal transplantation in children: preliminary experience in Paris.
PubMed:Food allergy and tacrolimus.
PubMed:Tacrolimus (FK506) and the pharmaceutical/academic/regulatory gauntlet.
PubMed:Roche, FDA announce new drug-interaction warnings for mibefradil.
PubMed:Immunoregulatory drugs: mechanistic basis for use in organ transplantation.
PubMed:Life-threatening food allergy in a child treated with FK506.
PubMed:Drug interactions and consequences of sodium restriction.
PubMed:Role of pharmacokinetic-pharmacodynamic principles in rational and cost-effective drug development.
PubMed:Immunosuppressants: cellular and molecular mechanisms of action.
PubMed:The use of therapeutic drug monitoring to optimise immunosuppressive therapy.
PubMed:Randomised trialomania? The multicentre liver transplant trials of tacrolimus.
PubMed:Expanding the kidney allograft donor pool in the tacrolimus era.
PubMed:FDA approved new drug bulletin: aprotinin injection (trasylol), tacrolimus (prograf).
PubMed:The interaction of immunosuppressive compounds in tandem stimulated peripheral human lymphocytes.
PubMed:FK506, artificial intelligence and pharmacoeconomics.
PubMed:Enhanced liver regeneration in rats treated with 15-deoxyspergualin alone and in combination with FK 506.
PubMed:Comparison of the in vitro and biophysical effects of cyclosporine A, FK-506, and mycophenolic acid on human peripheral blood lymphocytes.
 
Notes:
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