Details of the Drug

General Information of Drug (ID: DMXNZM4)

Drug Name

Oxazepam

Synonyms

Abboxampam; Abboxapam; Adumbran; Alepam; Ansioxacepam; Anxiolit; Aplakil; Astress; Azutranguil; Azutranquil; Bonare; Drimuel; Droxacepam; Durazepam; Hilong; Isodin; Lederpam; Limbial; Murelax; Nesontil; Noctazepam; Nortemazepam; Nozepam; Ossazepam; Oxanid; Oxazepamum; Oxazipam; Oxozepam; Pacienx; Praxiten; Propax; Psicopax; Psiquiwas; QUEN; Quilibrex; Rondar; Sedigoa; Serax; Serenal; Serenid; Serepax; Seresta; Serpax; Sigacalm; Sobril; Tacepam; Tarchomin; Tazepam; Uskan; Vaben; Zaxopam; Anxiolit retard; Ossazepam [DCIT]; P acienx; CB 8092; DF2371850; O5254_SIGMA; Wy 3498; Z 10 tr; Alepam (TN); Apo-astress; Hi-Long; Medopam (TN); Murelax (TN); N-Desmethyltemazepam; Noripam (TN); Oxa-puren; Oxazepamum [INN-Latin]; Purata (TN); Ro 5-6789; Serax (TN); Serenid-D; Serepax (TN); WY-3498; Wy-3498 stic; Z10-Tr; Ox-Pam (TN); Tranquo-buscopan-wirkstoff; Oxazepam (JAN/USP/INN); Oxazepam [USAN:INN:BAN:JAN]; (+-)-7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one; (+-)-Oxazepam; (RS)-Oxazepam; 1,3-Dihydro-7-chloro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one; 1,3-Dihydro-7-chloro-3-hydroxy-5-phenyl-3H-1,4-benzodiazepin-2-one; 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-1,4(2H)-benzodiazepin-2-one; 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepine-2-one; 7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Indication

Disease Entry	ICD 11	Status	REF
Alcohol withdrawal delirium	N.A.	Approved	[1]
Anxiety	N.A.	Approved	[1]
Anxiety disorder	6B00-6B0Z	Approved	[2]
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Therapeutic Class

Hypnotics and Sedatives

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

286.71

Logarithm of the Partition Coefficient (xlogp)

2.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 450,000 mg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 3 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability: 97% of drug becomes completely available to its intended biological destination(s) [5]
Clearance: The drug present in the plasma can be removed from the body at the rate of 1.1 mL/min/kg [6]
Elimination: Oxazepam is primarily eliminated in the urine as its glucuronide metabolite, with the feces containing approximately 21% of the unchanged drug [7]
Half-life: The concentration or amount of drug in body reduced by one-half in 8.2 hours [3]
Metabolism: The drug is metabolized via UGT2B15 [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.97544 micromolar/kg/day [8]
Unbound Fraction: The unbound fraction of drug in plasma is 0.04% [6]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.59 L/kg [6]
Water Solubility: The ability of drug to dissolve in water is measured as 0.045 mg/mL [4]

Chemical Identifiers

Formula: C15H11ClN2O2
IUPAC Name: 7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
Canonical SMILES: C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)O
InChI: InChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)
InChIKey: ADIMAYPTOBDMTL-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4616
ChEBI ID: CHEBI:7823
CAS Number: 604-75-1
DrugBank ID: DB00842
TTD ID: D09LDR
INTEDE ID: DR1214
ACDINA ID: D00499

Combinatorial Drugs (CBD)

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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
Translocator protein (TSPO)	TTPTXIN	TSPO_HUMAN	Agonist	[9]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[10]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[11]
Cytochrome P450 3A5 (CYP3A5)	DEIBDNY	CP3A5_HUMAN	Substrate	[12]
Cytochrome P450 3A7 (CYP3A7)	DERD86B	CP3A7_HUMAN	Substrate	[12]
UDP-glucuronosyltransferase 2B7 (UGT2B7)_{Main DME}	DEB3CV1	UD2B7_HUMAN	Substrate	[13]
Cytochrome P450 3A43 (CYP3A43)	DEO1IE3	CP343_HUMAN	Substrate	[12]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
UDP-glucuronosyltransferase 1A9	OTPCHAFX	UD19_HUMAN	Regulation of Drug Effects	[13]
UDP-glucuronosyltransferase 2B15	OTABTFU2	UDB15_HUMAN	Regulation of Drug Effects	[13]
UDP-glucuronosyltransferase 2B7	OT2Q71VQ	UD2B7_HUMAN	Biotransformations	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sodium bicarbonate	DMMU6BJ	Minor	Altered absorption of Oxazepam due to GI dynamics variation caused by Sodium bicarbonate.	Acidosis [5C73]	[15]
Oliceridine	DM6MDCF	Major	Additive CNS depression effects by the combination of Oxazepam and Oliceridine.	Acute pain [MG31]	[16]
Dihydrocodeine	DMB0FWL	Major	Additive CNS depression effects by the combination of Oxazepam and Dihydrocodeine.	Chronic pain [MG30]	[17]
Remifentanil	DMZTXCH	Major	Additive CNS depression effects by the combination of Oxazepam and Remifentanil.	Corneal disease [9A76-9A78]	[16]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Oxazepam and Esketamine.	Depression [6A70-6A7Z]	[18]
SODIUM CITRATE	DMHPD2Y	Minor	Altered absorption of Oxazepam due to GI dynamics variation caused by SODIUM CITRATE.	Discovery agent [N.A.]	[15]
Fosphenytoin	DMOX3LB	Moderate	Increased metabolism of Oxazepam caused by Fosphenytoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[19]
Didanosine	DMI2QPE	Minor	Altered absorption of Oxazepam due to GI dynamics variation caused by Didanosine.	Human immunodeficiency virus disease [1C60-1C62]	[15]
Probenecid	DMMFWOJ	Minor	Decreased metabolism of Oxazepam caused by Probenecid.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[20]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Oxazepam caused by PF-06463922 mediated induction of UGT.	Lung cancer [2C25]	[18]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Oxazepam and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[21]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Oxazepam and Lasmiditan.	Migraine [8A80]	[22]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Oxazepam and Flibanserin.	Mood disorder [6A60-6E23]	[23]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Oxazepam and Thalidomide.	Multiple myeloma [2A83]	[24]
Teduglutide	DMYOAKS	Moderate	Altered absorption of Oxazepam caused by Teduglutide.	Neonatal malabsorption syndrome [KB89]	[25]
Levomethadyl Acetate	DM06HG5	Major	Additive CNS depression effects by the combination of Oxazepam and Levomethadyl Acetate.	Opioid use disorder [6C43]	[17]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Oxazepam and Apraclonidine.	Optic nerve disorder [9C40]	[26]
Oxymorphone	DM65AGJ	Major	Additive CNS depression effects by the combination of Oxazepam and Oxymorphone.	Pain [MG30-MG3Z]	[16]
Diflunisal	DM7EN8I	Minor	Increased plasma concentration of Oxazepam and Diflunisal due to competitive binding of plasma proteins.	Pain [MG30-MG3Z]	[27]
Levorphanol	DMGS80V	Major	Additive CNS depression effects by the combination of Oxazepam and Levorphanol.	Pain [MG30-MG3Z]	[16]
Dezocine	DMJDB0Y	Major	Additive CNS depression effects by the combination of Oxazepam and Dezocine.	Pain [MG30-MG3Z]	[16]
Nalbuphine	DMOSQGU	Major	Additive CNS depression effects by the combination of Oxazepam and Nalbuphine.	Pain [MG30-MG3Z]	[16]
Buprenorphine	DMPRI8G	Major	Additive CNS depression effects by the combination of Oxazepam and Buprenorphine.	Pain [MG30-MG3Z]	[28]
Hydrocodone	DMQ2JO5	Major	Additive CNS depression effects by the combination of Oxazepam and Hydrocodone.	Pain [MG30-MG3Z]	[16]
Amiodarone	DMUTEX3	Minor	Potentiate the pharmacologic effects by the combination of Oxazepam and Amiodarone.	Ventricular tachyarrhythmia [BC71]	[29]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Butylparaben	E00142	7184	Antimicrobial preservative
D&C red no. 28	E00491	6097185	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
methylparaben	E00149	7456	Antimicrobial preservative
Propyl 4-hydroxybenzoate	E00141	7175	Antimicrobial preservative
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Carmellose sodium	E00625	Not Available	Disintegrant
Edetate calcium disodium	E00487	6093170	Complexing agent
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Lithol rubin BCA	E00607	135423095	Colorant
Magnesium stearate	E00208	11177	lubricant
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Sodium propionate	E00445	2723816	Antimicrobial preservative
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Oxazepam 10 mg capsule	10 mg	Oral Capsule	Oral
Oxazepam 30 mg capsule	30 mg	Oral Capsule	Oral
Oxazepam 15 mg capsule	15 mg	Oral Capsule	Oral

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References

1	Oxazepam FDA Label
2	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: 7253).
3	FDA Approved Drug Products: Oxazepam oral capsules
4	BDDCS applied to over 900 drugs
5	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7	Health Canada Product Monograph: Oxazepam oral tablets
8	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9	Effects of the combination of metyrapone and oxazepam on cocaine and food self-administration in rats. Pharmacol Biochem Behav. 2008 Nov;91(1):181-9.
10	Bioreactor systems in drug metabolism: synthesis of cytochrome P450-generated metabolites. Metab Eng. 2000 Apr;2(2):115-25.
11	Evidence for oxazepam as an in vivo probe of UGT2B15: oxazepam clearance is reduced by UGT2B15 D85Y polymorphism but unaffected by UGT2B17 deletion. Br J Clin Pharmacol. 2009 Nov;68(5):721-30.
12	Cytochrome P450 enzyme activity and protein expression in primary porcine enterocyte and hepatocyte cultures. Xenobiotica. 2000 Jan;30(1):27-46.
13	Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos. 2002 Nov;30(11):1257-65.
14	(S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7. Pharmacogenetics. 1995 Feb;5(1):43-9. doi: 10.1097/00008571-199502000-00005.
15	Chun AH, Carrigan PJ, Hoffman DJ, Kershner RP, Stuart JD "Effect of antacids on absorption of clorazepate." Clin Pharmacol Ther 22 (1977): 329-35. [PMID: 19188]
16	US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
17	US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
18	Cerner Multum, Inc. "Australian Product Information.".
19	Backman JT, Olkkola KT, Ojala M, Laaksovirta H, Neuvonen PJ "Concentrations and effects of oral midazolam are greatly reduced in patients treated with carbamazepine or phenytoin." Epilepsia 37 (1996): 253-7. [PMID: 8598183]
20	Abernethy DR, Greenblatt DJ, Ameer B, Shader RI "Probenecid impairment of acetaminophen and lorazepam clearance: direct inhibition of ether glucuronide formation." J Pharmacol Exp Ther 234 (1985): 345-9. [PMID: 4020675]
21	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
22	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
23	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
24	Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.
25	Product Information. Gattex (teduglutide). NPS Pharmaceuticals, Bedminster, NJ.
26	Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
27	van Hecken AM, Tjandramaga TB, Verbesselt R, de Schepper PJ "The influence of diflunisal on the pharmacokinetics of oxazepam." Br J Clin Pharmacol 20 (1985): 225-34. [PMID: 4041343]
28	Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]
29	Kerin NZ, Aragon E, Faitel K, Frumin H, Rubenfire M "Long-term efficacy and toxicity of high- and low-dose amiodarone regimens." J Clin Pharmacol 29 (1989): 418-23. [PMID: 2661600]