Details of the Drug

General Information of Drug (ID: DMDBWHY)

Drug Name

Heroin diacetylmorphine

Synonyms

Diamorphine (TN)

Indication

Disease Entry	ICD 11	Status	REF
Neurological disorder	6B60	Approved	[1]

Affected Organisms

Humans and other mammals

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

369.4

Logarithm of the Partition Coefficient (xlogp)

1.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: The bioavailability of drug is 29-77% [2]
Clearance: The clearance of drug is 8.7 +/- 2.6 L/min [3]
Elimination: The majority of the drug is excreted via the kidney as glucuronides and to a much lesser extent as morphine, and about 7-10 % is eliminated via the biliary system into the faeces [4]
Metabolism: The drug is metabolized via various esterase enzymes [5]

Chemical Identifiers

Formula: C21H23NO5
IUPAC Name: [(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
Canonical SMILES: CC(=O)O[C@H]1C=C[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)OC(=O)C)CCN3C
InChI: InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
InChIKey: GVGLGOZIDCSQPN-PVHGPHFFSA-N

Cross-matching ID

PubChem CID: 5462328
ChEBI ID: CHEMBL27808
CAS Number: 561-27-3
UNII: 70D95007SX
DrugBank ID: DB01452
TTD ID: D0T6WT
INTEDE ID: DR0807

Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Acetylcholinesterase (ACHE)_{Main DME}	DEQ2BAJ	ACES_HUMAN	Substrate	[6]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
5-hydroxymethyl-dUMP N-hydrolase (DNPH1)	OTEZVTI1	DNPH1_HUMAN	Gene/Protein Processing	[7]
Adropin (ENHO)	OT91QASK	ENHO_HUMAN	Gene/Protein Processing	[7]
Alpha-actinin-2 (ACTN2)	OT9FOLD7	ACTN2_HUMAN	Gene/Protein Processing	[7]
Amphiphysin (AMPH)	OTWPGWZX	AMPH_HUMAN	Gene/Protein Processing	[7]
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Gene/Protein Processing	[7]
Biogenesis of lysosome-related organelles complex 1 subunit 6 (BLOC1S6)	OT96NE03	BL1S6_HUMAN	Gene/Protein Processing	[7]
Ceramide glucosyltransferase	OTRT5P5I	CEGT_HUMAN	Gene/Protein Processing	[7]
Cocaine esterase (CES2)	OTC647SQ	EST2_HUMAN	Biotransformations	[8]
D(2) dopamine receptor (DRD2)	OTBLXKEG	DRD2_HUMAN	Gene/Protein Processing	[9]
Deformed epidermal autoregulatory factor 1 homolog (DEAF1)	OTCLX3ZW	DEAF1_HUMAN	Gene/Protein Processing	[7]

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 Heroin diacetylmorphine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Oliceridine	DM6MDCF	Major	Additive CNS depression effects by the combination of Heroin diacetylmorphine and Oliceridine.	Acute pain [MG31]	[10]
Dihydrocodeine	DMB0FWL	Major	Additive CNS depression effects by the combination of Heroin diacetylmorphine and Dihydrocodeine.	Chronic pain [MG30]	[10]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Heroin diacetylmorphine and Esketamine.	Depression [6A70-6A7Z]	[11]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of lowers seizure threshold by the combination of Heroin diacetylmorphine and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[12]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Heroin diacetylmorphine and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[13]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Heroin diacetylmorphine and Lasmiditan.	Migraine [8A80]	[14]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Heroin diacetylmorphine and Flibanserin.	Mood disorder [6A60-6E23]	[14]


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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64.
3	Halbsguth U, Rentsch KM, Eich-Hochli D, Diterich I, Fattinger K: Oral diacetylmorphine (heroin) yields greater morphine bioavailability than oral morphine: bioavailability related to dosage and prior opioid exposure. Br J Clin Pharmacol. 2008 Dec;66(6):781-91. doi: 10.1111/j.1365-2125.2008.03286.x.
4	Electronic Medicines Compendium: Diamorphine Hydrochloride BP 100 mg Lyophilisate for Solution for Injection Monograph
5	Huecker MR, Marraffa J. Heroin. [Updated 2018 Oct 27]. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2018 Jan.
6	Kinetic characterization of cholinesterases and a therapeutically valuable cocaine hydrolase for their catalytic activities against heroin and its metabolite 6-monoacetylmorphine. Chem Biol Interact. 2018 Sep 25;293:107-114.
7	Distinctive profiles of gene expression in the human nucleus accumbens associated with cocaine and heroin abuse. Neuropsychopharmacology. 2006 Oct;31(10):2304-12. doi: 10.1038/sj.npp.1301089. Epub 2006 May 3.
8	Contribution of human esterases to the metabolism of selected drugs of abuse. Toxicol Lett. 2015 Jan 5;232(1):159-66. doi: 10.1016/j.toxlet.2014.10.026. Epub 2014 Oct 24.
9	Dopamine D1 receptor protein is elevated in nucleus accumbens of human, chronic methamphetamine users. Mol Psychiatry. 2000 Nov;5(6):664-72. doi: 10.1038/sj.mp.4000760.
10	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.".
11	Product Information. Spravato (esketamine). Janssen Pharmaceuticals, Titusville, NJ.
12	Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
13	Gilman AG, Rall TW, Nies AS, Taylor P, eds. "Goodman and Gilman's the Pharmacological Basis of Therapeutics. 8th ed." New York, NY: Pergamon Press Inc. (1990):.
14	Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]