pimecrolimus

Also known as ASM981, SDZ ASM 981, SDZ-ASM 981, 33-epi-chloro-33-desoxyascomycin

Pimecrolimus is an immunosuppressant drug of the calcineurin inhibitor class used in the treatment of atopic dermatitis (eczema).

Key facts

Drug.IUPAC_name: (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-3-{(E)-2-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]-1-methylvinyl}-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosin-1,7,20,21(4H,23H)-tetrone
Drug.image: Pimecrolimus.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Pimecrolimus ball-and-stick.png
Drug.image_class2: bg-transparent
Drug.tradename: Elidel
Drug.pregnancy_AU: B3
Drug.pregnancy_US: C
Drug.legal_US: Rx-only
Drug.routes_of_administration: topical
Drug.class: immunosuppressant
Drug.bioavailability: low systemic absorption
Drug.protein_bound: 74%–87%
Drug.metabolism: Hepatic CYP3A
Drug.CAS_number: 137071-32-0
Drug.ATC_prefix: D11
Drug.ATC_suffix: AH02

via Wikipedia infobox

Chemical data

Formula: C43H68ClNO11
Molecular weight: 810.4 g/mol
IUPAC name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(E)-1-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
SMILES: CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@@H]([C@@H](C4)OC)Cl)/C)O)C)OC)OC)C)\C
InChIKey: KASDHRXLYQOAKZ-XDSKOBMDSA-N
XLogP: 3.8
Polar surface area: 158 Å²
H-bond donors: 2
H-bond acceptors: 11
Formal charge: 0

via PubChem

Research

1,104 papers

Pimecrolimus: a review.Journal of the European Academy of Dermatology and Venereology : JEADV · 2003
Off-label Uses of Topical Pimecrolimus.Journal of cutaneous medicine and surgery · 2019
Safety and efficacy of pimecrolimus in atopic dermatitis: a 5-year randomized trial.Pediatrics · 2015
Pimecrolimus in dermatology.Giornale italiano di dermatologia e venereologia : organo ufficiale, Societa italiana di dermatologia e sifilografia · 2009
Pimecrolimus 1% cream for mild-to-moderate atopic dermatitis: a systematic review and meta-analysis with a focus on children and sensitive skin areas.European journal of dermatology : EJD · 2023

via PubMed

Wikidata facts

Mass: 809.448

Show 5 more facts

chemical formula: C₄₃H₆₈ClNO₁₁
World Health Organisation international non-proprietary name: pimecrolimus
isomeric SMILES: CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@@H]([C@@H](C4)OC)Cl)/C)O)C)OC)OC)C)\C
canonical SMILES: CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)Cl)C)O)C)OC)OC)C)C
Commons category: Pimecrolimus

Sources (5)

via Wikidata · CC0

~6 min read

Article

7 sections

Contents

Medical uses
Atopic dermatitis
Side effects
Pharmacology
Development and production
References
External links

{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464206673 | IUPAC_name = (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-3-{(E)-2-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]-1-methylvinyl}-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosin-1,7,20,21(4H,23H)-tetrone | image = Pimecrolimus.svg | image_class = skin-invert-image | width = 200 | image2 = Pimecrolimus ball-and-stick.png | image_class2 = bg-transparent