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).

In the Vinony graph

Within Vinony's link graph, pimecrolimus is referenced by 262 other articles, and connects out to immunosuppressive drug, lithium and United Kingdom.

It is catalogued under topics including Disulfiram-like drugs, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.

Its subject is documented across 20 Wikipedia language editions.

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

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2001
Admin. routes: topical
Indications: atopic eczema, Eczematoid dermatitis, Vitiligo, lichen planus

via ChEMBL · EBI

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

Subclass of: chemical compound
Mass: 809.448
Has use: medication

Show 7 more facts

chemical formula: C₄₃H₆₈ClNO₁₁
World Health Organisation international non-proprietary name: pimecrolimus
medical condition treated: atopic dermatitis
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
legal status (medicine): boxed warning

Sources (5)

via Wikidata · CC0

~6 min read

Encyclopedic overview

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

Excerpted from Wikipedia’s “pimecrolimus” article, available under the CC BY-SA 4.0 licence.