Rx00244 - Tretinoin


Name:
Tretinoin
Rx ID:
Rx00244
Validation Level:
Phenomic Similarity:
0.526
Reference ID:
DB00755
Primary Indications:
French-American-British acute promyelocytic leukemia classification M3; acne vulgaris; flat warts; psoriasis; ichthyosis congenita; icthyosis vulgaris; lamellar icthyosis; keratosis palmaris et plantaris; epidermolytic hyperkeratosis; senile comedones; senile keratosis; keratosis follicularis; Darier's disease; basal cell carcinomas; photodamage
Orphan Indications:
No annotated orphan indications.
Rare Indications:
Squamous metaplasia of the ocular surface epithelia; mucous deficiency; keratinization; acute leukemia; chronic leukemia; T-cell, non-Hodgkin's lymphoma
Common Indications:
Acute promyelocytic leukemia
Drug Interactions:
Atazanavir; Carbamazepine; Celecoxib; Demeclocycline; Desogestrel; Doxycycline; Drospirenone; Eltrombopag; Ethinyl Estradiol; Ethynodiol; ...
Click to show more...
Food Interactions:
No annotated food interactions in DrugBank.

Interactive 3D Model

Interactive Drug Target Network

Interactive Bipartite Drug Repurposing Graph

Rx00244
Primary Indication
Secondary Indication

Visualize Chemical Properties

Select x-axis

Select y-axis

Disease prevalence from Electronic Health Records

Click row to show all

Disease A Disease B A∩B A∩¬B B∩¬A Odds-Ratio P-Value Adjusted P-Value
senile comedones mucous deficiency 1143 16665 29525 9.373 0 0.0
acne vulgaris mucous deficiency 1143 16665 29525 9.373 0 0.0
French-American-British acute promyelocytic leukemia classification M3 acute promyelocytic leukemia 941 941 941 4287.911 0 0.0
psoriasis mucous deficiency 545 9320 29525 7.991 1.85E-280 5.94e-277
flat warts mucous deficiency 260 2463 29525 14.426 3.54E-193 1.14e-189
keratosis palmaris et plantaris mucous deficiency 186 1831 29525 13.883 3.99E-136 1.28e-132
keratosis follicularis mucous deficiency 186 2739 29525 9.28 9.20E-108 2.96e-104
Darier's disease mucous deficiency 186 2739 29525 9.28 9.20E-108 2.96e-104
basal cell carcinomas T-cell, non-Hodgkin's lymphoma 141 6075 6716 13.944 1.61E-105 5.17e-102
senile keratosis mucous deficiency 278 8310 29525 4.572 7.44E-90 2.39e-86
photodamage mucous deficiency 60 3124 29525 2.625 1.02E-10 3.26e-07

Shared Genetic Architectures of Disease Pairs

Click row to show all

Disease A Disease B Adjusted P-Value Shared Gene IDs
PSORIASIS ACUTE LEUKEMIA 4.07e-27 3807, ABCB1, ABCC1, ABCF1, ABCG2, ABHD16A, ACE, ADAM33, AGT, ALOX12, ALOX15, APOE, BAG6, BAK1, BDNF, C2, C6orf15, CARD8, CCL2, CCR1, CCR2, CCR4, CCR5, CD14, CD28, CD40, CFB, COL11A2, CRP, CTLA4, CX3CR1, CYP1A1, CYP1A2, CYP2C19, DAXX, DDR1, DEFB1, DHFR, EDN1, EGF, ERCC2, FCGR2A, FCGR3A, FCGR3B, FGF1, FGF2, FOXP3, FPGS, GGH, GPX1, GSTM1, GSTP1, GSTT1, HFE, HLA-A, HLA-B, HLA-C, HLA-DMB, HLA-DOA, HLA-DPA1, HLA-DPB1, HLA-DQA1, HLA-DQB1, HLA-DRB1, HLA-DRB3, HLA-DRB4, HLA-E, HLA-G, HSPA1A, HSPA1B, HSPA1L, IER3, IFNG, IKZF3, IL10, IL12A, IL12B, IL12RB1, IL12RB2, IL13, IL15, IL17A, IL17F, IL19, IL1A, IL1B, IL1R1, IL1RAP, IL1RN, IL2, IL21, IL22, IL22RA2, IL23R, IL2RA, IL4, IL4R, IL6, IL6R, IL8, IRAK1, IRF1, IRF5, JAK2, KIF5A, KIR2DL1, KIR2DL2, KIR2DL3, KIR2DL4, KIR2DL5A, KIR2DL5B, KIR2DP1, KIR2DS1, KIR2DS2, KIR2DS3, KIR2DS4, KIR2DS5, KIR3DL1, KIR3DL2, KIR3DL3, KIR3DP1, KIR3DS1, KLRC4, LAG3, LEP, LST1, LTA, MBL2, MDC1, MDM2, MEFV, MICA, MIF, MIR146A, MMP2, MTHFR, NAT2, NFKB1, NFKBIA, NFKBIL1, NLRP1, NOD2, NOS2, NOS3, NOTCH2, NOTCH4, NQO1, NR3C1, PON1, PTPN22, RAD50, REL, REV3L, RFC1, RUNX1, SLC22A4, SLC6A4, SOCS1, SOD2, STAT2, STAT3, STAT4, STK19, TAP1, TAP2, TGFB1, TLR10, TLR2, TLR4, TLR9, TNF, TNFAIP3, TNFRSF10A, TNFRSF11A, TNFRSF1A, TNFRSF1B, TNFRSF9, TNIP1, TP53, TRAF1, TRIM27, TSC1, TYK2, TYMS, VDR, VEGFA
BASAL CELL CARCINOMAS ACUTE LEUKEMIA 2.89e-18 ACE, BRAF, BRCA1, BRCA2, CAT, CCND1, CD3EAP, CDKN1A, CDKN2A, CDKN2B, CLPTM1L, CTLA4, CTNNB1, CYP1A1, CYP2D6, EGFR, ERCC1, ERCC2, ERCC6, FAS, FASLG, FGFR2, GLI1, GPX1, GSTA4, GSTM1, GSTM3, GSTO2, GSTP1, GSTT1, HFE, HLA-DRB1, IFNG, IL10, IL12A, IL1A, IL1B, IL1RN, IL2, IL4, IL6, IL8, IRF4, LIG4, MDM2, MICA, MIR146A, MMP3, MMP8, MMP9, MTHFR, NBN, PTCH1, PTGS2, RNASEL, TERT, TLR4, TNF, TP53, TP53BP1, VDR, XPA, XPC, XRCC1, XRCC2, XRCC3

Chemical, Pharmacological and Biological Annotations


ATC Code:
D10AD01; D10AD51; L01XX14; D10BA01 D10AD04;
Brands:
Aberel (Janssen); Aberela (Janssen); Airol (Pierre Fabre Dermo); Dermairol (Roche); Eudyna (Zydus); Kétrel (Bailleul); Retisol-A (Stiefel); Sotret (Ranbaxy Laboratories Inc.); Stieva-A (Stiefel); Vitinoin
Categories:
Antineoplastic Agents; Keratolytic Agents
ChEBI ID:
15367
PubChem ID:
444795
KEGG Drug ID:
D00094
SMILE:
CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O
InChI:
1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
Classification:
Kingdom:
Organic Compounds
Superclass:
Lipids
Class:
Prenol Lipids
Subclass:
Retinoids
Indication:
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 condit...
Click to show more...
Pharmacodynamics:
Tretinoin, also known as all-<i>trans</i>-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and ar...
Click to show more...
Description:
Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used ...
Click to show more...
Mechanism:
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...
Click to show more...

Adsorption, Distribution, Metabolism, Excretion and Toxicity


Human Intestinal Absorption:
+
Blood Brain Barrier:
+
Caco-2 permeable:
+
P-glycoprotein substrate:
Non-substrate
P-glycoprotein inhibitor I:
Non-inhibitor
P-glycoprotein inhibitor II:
Non-inhibitor
Renal organic cation transporter:
Non-inhibitor
CYP450 2C9 substrate:
Non-inhibitor
CYP450 2D6 substrate:
Non-inhibitor
CYP450 2C19 substrate:
Non-inhibitor
CYP450 inhibitory promiscuity:
Low CYP Inhibitory Promiscuity
Ames test:
Non AMES toxic
Carcinogenicity:
Non-carcinogens
Biodegradation:
Ready biodegradable
Rat acute toxicity:
2.1455 LD50, mol/kg
hERG inhibition (predictor I):
Weak inhibitor
hERG inhibition (predictor II):
Non-inhibitor

Contact Us:
Please contact us if you have questions or comments about RepurposeDB. You can also contact us if you need help in submitting your drug repositioning investigation to RepurposeDB.


Dudley Laboratory
Department of Genetics and Genomic Sciences
Icahn Institute for Genomics and Multiscale Biology
Icahn School of Medicine at Mount Sinai
One Gustave L. Levy Place, Box 1498
Manhattan, New York City, NY
repurposedb@dudleylab.org