Details of the Drug

General Information of Drug (ID: DMJ2AH4)

Drug Name

Vitamin A

Synonyms

Retinol; retinol; all-trans-Retinol; 68-26-8; Vitamin A1; Alphalin; Axerophthol; Afaxin; Oleovitamin A; Chocola A; Ophthalamin; Epiteliol; Biosterol; Aquasynth; Apostavit; Alphasterol; Veroftal; Testavol; Anatola; Prepalin; Myvpack; Agoncal; Agiolan; Vogan; Axerol; Vitpex; Avibon; Apexol; Aoral; Vaflol; Dofsol; Avitol; Vitamin A alcohol; Disatabs Tabs; Lard Factor; Bentavit A; Dohyfral A; all-trans-Retinyl alcohol; Alcovit A; Vogan-Neu; Anatola A; Plivit A; A-Mulsal; Vi-Alpha; A-Vitan; All-trans retinol; Atars; Vafol; trans-retinol; all-trans-Vitamin A; ACON; ATAV; Alin; Avita; Axerophtholum; Cylasphere; LPK; Retinolo; Retinolum; TROL; Thalasphere; Wachstumsvitamin; All Trans Retinol; Antixerophthalmic vitamin; Antixerophthalmisches Vitamin; Aquasol A Parenteral; Homagenets Aoral; Homagenets aorl; Hydrovit A; Mvc Plus; Retinol solution; Retinolo [DCIT]; Retrovitamin A; Sehkraft A; Super A; Testavol S; Vitamin A cryst; Vitamine A; Vitaminum A; Vitavel A; Zinosan N; Rovimix A 500; Vitamin A1 alcohol; A-Sol; Anti-infective vitamin; Beta-Retinol; Retinol [INN:BAN]; Retinolum [INN-Latin]; Solu-A; Trans-Vitamin A alcohol; Trans-retinol; Vi-a; Vi-alpha; Vio-A; Vitamin A (Feed); Vitamin A (USP); Vitamin A alcohol (VAN); Vitamin A1 alcohol, all trans; Vitamin-A; Vitamin-A alcohol; Vitamin-A alcohol solution; Vitamin-A1; Vitavel-A; Vogan-nu; A-Vi-Pel; ALL-TRANS RETINOL (SEE ALSO RETINOID PROJECT 1); All-trans-Retinol; All-trans-Retinyl alcohol; All-trans-Vitamin A; All-trans-Vitamin A alcohol; All-trans-Vitamin A1; Del-VI-A; Hi-A-Vita; Nio-A-Let; Ro-a-vit; Trans-Retinol acid (Vitamin A); Vi-Dom-A; [11,12-3H]-Retinol; MVC 9+3; MVI-12; Retinol, all-trans-(8CI); Retin-11,12-t2-ol (9CI); Retinol-(cellular-retinol-binding-protein); Alcohol 9,13-dimethyl-7-(1,1,5-trimethyl-6-cyclohexen-5-yl)-7,9,11,13-nonatetraen-15-ol; All-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclchexen-1-yl)-2,4,6,8-nonatetraen-1-ol; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonate-traen-1-ol; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol; 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)-Isomer; Tricyclics

Indication

Disease Entry	ICD 11	Status	REF
Night blindness	9D45	Approved	[1]
Vitamin A deficiency	N.A.	Approved	[2]
Vitamin deficiency	5B55-5B71	Approved	[2]
Kinetoplastids	1F61-1G2Z	Investigative	[3]
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Therapeutic Class

Vitamins

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

286.5

Logarithm of the Partition Coefficient (xlogp)

5.7

Rotatable Bond Count (rotbonds)

5

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

1

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Elimination: 0% of drug is excreted from urine in the unchanged form [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.9 hours [5]
Metabolism: The drug is metabolized via the hepatic []
Water Solubility: The ability of drug to dissolve in water is measured as 0.044 mg/mL [4]

Chemical Identifiers

Formula: C20H30O
IUPAC Name: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
Canonical SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C
InChI: InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChIKey: FPIPGXGPPPQFEQ-OVSJKPMPSA-N

Cross-matching ID

PubChem CID: 445354
ChEBI ID: CHEBI:17336
CAS Number: 11103-57-4
DrugBank ID: DB00162
TTD ID: D0S7WX
INTEDE ID: DR1699

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Retinoic acid receptor (RAR)	TTOD7B3	NOUNIPROTAC	Binder	[6]
Retinoic acid receptor RXR-gamma (RXRG)	TTH029C	RXRG_HUMAN	Binder	[6]
Trypanosoma Trypanothione reductase (Trypano TPR)	TTRTKPV	TYTR_TRYBB	Binder	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[7]
Cytochrome P450 2E1 (CYP2E1)	DEVDYN7	CP2E1_HUMAN	Substrate	[8]
Cytochrome P450 1A2 (CYP1A2)	DEJGDUW	CP1A2_HUMAN	Substrate	[9]
Cytochrome P450 1B1 (CYP1B1)	DE9QHP6	CP1B1_HUMAN	Substrate	[10]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[11]
Retinoic acid 4-hydroxylase 26A1 (CYP26A1)	DEOVJF2	CP26A_HUMAN	Substrate	[12]
Retinal dehydrogenase 2 (ALDH1A2)	DEKN1H4	AL1A2_HUMAN	Substrate	[13]
Retinol dehydrogenase 5 (RDH5)	DESI4OK	RDH5_HUMAN	Substrate	[14]
Cytochrome P450 2S1 (CYP2S1)	DE6NMGO	CP2S1_HUMAN	Substrate	[15]
Short-chain dehydrogenase/reductase retSDR8 (DHRS9)	DEGTU5I	DHRS9_HUMAN	Substrate	[13]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Protein Interaction/Cellular Processes	[16]
Aldo-keto reductase family 1 member B1 (AKR1B1)	OTRX72TH	ALDR_HUMAN	Drug Response	[17]
Aldo-keto reductase family 1 member B10 (AKR1B10)	OTOA4HTH	AK1BA_HUMAN	Drug Response	[17]
Angiotensin-converting enzyme 2 (ACE2)	OTTRZGU7	ACE2_HUMAN	Gene/Protein Processing	[18]
Apolipoprotein D (APOD)	OTT77XW8	APOD_HUMAN	Protein Interaction/Cellular Processes	[19]
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[20]
Cadherin-1 (CDH1)	OTFJMXPM	CADH1_HUMAN	Gene/Protein Processing	[21]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[22]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[23]
Cellular retinoic acid-binding protein 2 (CRABP2)	OTY01V9G	RABP2_HUMAN	Gene/Protein Processing	[24]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Night blindness

ICD Disease Classification

9D45

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Retinoic acid receptor RXR-gamma (RXRG)	DTT	RXRG	4.44E-02	-0.25	-0.41
Cytochrome P450 2E1 (CYP2E1)	DME	CYP2E1	1.17E-01	1.32E-01	3.15E-01
Retinol dehydrogenase 5 (RDH5)	DME	RDH5	3.70E-03	-9.68E-01	-9.05E-01
Cytochrome P450 2C8 (CYP2C8)	DME	CYP2C8	5.27E-01	-1.74E-02	-6.97E-02
Retinoic acid 4-hydroxylase 26A1 (CYP26A1)	DME	CYP26A1	1.49E-03	-6.33E-01	-1.14E+00
Retinal dehydrogenase 2 (ALDH1A2)	DME	ALDH1A2	7.25E-02	-2.14E-01	-3.49E-01
Cytochrome P450 1A2 (CYP1A2)	DME	CYP1A2	4.89E-02	-3.74E-01	-6.96E-01
Short-chain dehydrogenase/reductase retSDR8 (DHRS9)	DME	DHRS9	1.77E-01	-2.11E-01	-5.22E-01
Cytochrome P450 1B1 (CYP1B1)	DME	CYP1B1	5.37E-06	-1.40E+00	-1.52E+00
Cytochrome P450 2S1 (CYP2S1)	DME	CYP2S1	1.29E-01	-3.58E-01	-7.51E-01
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	1.10E-01	-1.23E-01	-2.88E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Vitamin A (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Tretinoin	DM49DUI	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Tretinoin.	Acne vulgaris [ED80]	[25]
Isotretinoin	DM4QTBN	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Isotretinoin.	Acne vulgaris [ED80]	[25]
Sarecycline	DMLZNIQ	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Sarecycline .	Acne vulgaris [ED80]	[26]
Oxytetracycline	DMOVH1M	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Oxytetracycline.	Bacterial infection [1A00-1C4Z]	[26]
Omadacycline	DMR2J95	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Omadacycline.	Bacterial infection [1A00-1C4Z]	[26]
Minocycline	DMVN5OH	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Minocycline.	Bacterial infection [1A00-1C4Z]	[26]
Tetracycline	DMZA017	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Tetracycline.	Bacterial infection [1A00-1C4Z]	[26]
Demeclocycline	DMZEPFJ	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Demeclocycline.	Bronchitis [CA20]	[26]
TP-434	DM5A31S	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and TP-434.	Infectious gastroenteritis/colitis [1A40]	[26]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Vitamin A caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[25]
Orlistat	DMRJSP8	Minor	Decreased absorption of Vitamin A caused by Orlistat.	Obesity [5B80-5B81]	[27]
Doxycycline	DM7ICNU	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Doxycycline.	Periodontal disease [DA0C]	[26]
Acitretin	DM8BKU9	Major	Increased risk of pseudotumor cerebri by the combination of Vitamin A and Acitretin.	Psoriasis [EA90]	[25]
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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4053).
2	Vitamin A FDA Label
3	Opportunities and challenges in antiparasitic drug discovery. Nat Rev Drug Discov. 2005 Sep;4(9):727-40.
4	BDDCS applied to over 900 drugs
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Vitamins and cofactors: highlights of ESBOC 2009. Nat Chem Biol. 2009 Aug;5(8):530-3.
7	Biosynthesis of all-trans-retinoic acid from all-trans-retinol: catalysis of all-trans-retinol oxidation by human P-450 cytochromes. Drug Metab Dispos. 2000 Mar;28(3):315-22.
8	The role of inflammatory cells and cytochrome P450 in the potentiation of CCl4-induced liver injury by a single dose of retinol. Toxicol Appl Pharmacol. 1996 Dec;141(2):507-19.
9	Carotenoids as regulators for inter-species difference in cytochrome P450 1A expression and activity in ungulates and rats. Food Chem Toxicol. 2010 Nov;48(11):3201-8.
10	Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7.
11	Effects of arachidonic acid, prostaglandins, retinol, retinoic acid and cholecalciferol on xenobiotic oxidations catalysed by human cytochrome P450 enzymes. Xenobiotica. 1999 Mar;29(3):231-41.
12	Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Mol Pharmacol. 2015;87(3):430-41.
13	Vitamin A metabolism by dendritic cells triggers an antimicrobial response against Mycobacterium tuberculosis. mSphere. 2019 Jun 5;4(3). pii: e00327-19.
14	Generation of retinaldehyde for retinoic acid biosynthesis. Biomolecules. 2019 Dec 18;10(1). pii: E5.
15	The involvement of cytochrome p450 (CYP) 26 in the retinoic acid metabolism of human epidermal keratinocytes. Biochim Biophys Acta. 2009 Mar;1791(3):220-8.
16	Retinol and retinoic acid bind human serum albumin: stability and structural features. Int J Biol Macromol. 2007 Apr 10;40(5):484-90. doi: 10.1016/j.ijbiomac.2006.11.005. Epub 2006 Nov 24.
17	Aldo-keto reductases from the AKR1B subfamily: retinoid specificity and control of cellular retinoic acid levels. Chem Biol Interact. 2009 Mar 16;178(1-3):171-7. doi: 10.1016/j.cbi.2008.10.027. Epub 2008 Oct 25.
18	Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
19	Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. doi: 10.1016/j.bbapap.2005.12.006. Epub 2006 Jan 6.
20	Vitamin A supplementation reduces the monocyte chemoattractant protein-1 intestinal immune response of Mexican children. J Nutr. 2006 Oct;136(10):2600-5. doi: 10.1093/jn/136.10.2600.
21	Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells. Arch Biochem Biophys. 2006 Nov 1;455(1):48-60.
22	Elucidation of apoptosis induced by serum deprivation in cultured conjunctival epithelial cells. Br J Ophthalmol. 2006 Jun;90(6):760-4. doi: 10.1136/bjo.2005.088203. Epub 2006 Mar 10.
23	Retinol decreases beta-catenin protein levels in retinoic acid-resistant colon cancer cell lines. Mol Carcinog. 2007 Apr;46(4):315-29. doi: 10.1002/mc.20280.
24	Molecular and metabolic retinoid pathways in human amniotic membranes. Biochem Biophys Res Commun. 2006 Aug 11;346(4):1207-16. doi: 10.1016/j.bbrc.2006.06.024. Epub 2006 Jun 12.
25	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
26	Lewis PA, Kearney PJ "Pseudotumor cerebri induced by minocycline treatment for acne vulgaris." Acta Derm Venereol 77 (1997): 83. [PMID: 9059695]
27	Product Information. Xenical (orlistat). Roche Laboratories, Nutley, NJ.