3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

HCID 5538

Grundinformationen

Standard-SMILES
CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(=O)O
InChIKey
SHGAZHPCJJPHSC-UHFFFAOYSA-N
Summenformel
C20H28O2
Durchschnittliche Molmasse
300,4 g/mol

Überblick

Retinoic acid is a retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified). It has a role as a human metabolite. It is a retinoid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a retinoate.

Namen und Bezeichner

Bevorzugter Name
3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
IUPAC
3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid

Namen und Synonyme

3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acidRefChem:106615311-cis Retinoic Acid3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acidTretinoina (INN-Spanish)Tretinoina [INN-Spanish]Avita (0.025% gel)retinylpalmitats1653LGD 100057Spectrum_001676
Weitere Namen anzeigen
SpecPlus_000696Prestwick0_000256Prestwick0_000257Prestwick1_000256Prestwick1_000257Spectrum2_001983Spectrum3_001793Spectrum4_000901

Datenbank-Bezeichner

PubChem CID
5538
ChEMBL
CHEMBL1235644
ChEBI
CHEBI:26536

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,3
Polarare Oberfläche (TPSA)
37,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
5
Schwere Atome
22

Experimentelle und physikochemische Eigenschaften

LogP6.3

Sicherheit und Regulatorisches

Toxikologische Informationen

Exposure Routes1-31% (topical)
Toxicity Summary · 1 Eintrag

Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesHepatic Half Life: 0.5-2 hours

Verwendung und Herstellung

Uses · 1 Eintrag

For the the induction of remission in patients with acute promyelocytic leukemia (APL), French-American-British (FAB) classification M3 (including the M3 variant); For the topical treatment of acne vulgaris, flat warts and other skin conditions (psoriasis, ichthyosis congenita, icthyosis vulgaris, lamellar icthyosis, keratosis palmaris et plantaris, epidermolytic hyperkeratosis, senile comedones, senile keratosis, keratosis follicularis (Darier's disease), and basal cell carcinomas.); For palliative therapy to improve fine wrinkling, mottled hyperpigmentation, roughness associated with photodamage.

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