Diacetylmorphine

Summary

Diacetylmorphine (CHEMBL459324) is a phase-3 clinical-stage small-molecule opioid analgesic; indicated across 3 conditions including heroin dependence and opiate dependence.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Indications: 3 conditions
• Clinical trials: 7
• Chemistry: 369.4 Da · C21H23NO5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL459324
Name	Diacetylmorphine
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	5462328
ChEBI	CHEBI:27808
Molecular formula	C21H23NO5
Molecular weight	369.4
InChIKey	GVGLGOZIDCSQPN-PVHGPHFFSA-N

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

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

ChEBI definition: A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.

Pharmacological roles (ChEBI): opioid analgesic, μ-opioid receptor agonist, prodrug.

Also known as: Diacetylmorphine, IDS-NH-001, IDS-NH-001(SECT.3), J6.494G, heroin, Heroin, SID144206165, DIACETYLMORPHINE

Parent form; salt/anhydrous children: CHEMBL2106627

Patent coverage: 12,720 distinct patent families (43,123 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 43,122 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

No target linkage available.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

3 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
heroin dependence	3	MONDO:0005367	EFO:0004240
opiate dependence	3	MONDO:0005530	EFO:0005611

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 7.

Phase distribution

Phase	Trials
PHASE3	3
PHASE2	2
PHASE1	1
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00268814	PHASE3	COMPLETED	The German Project of Heroin Assisted Treatment of Opiate Dependent Patients
NCT00710385	PHASE3	COMPLETED	Abuse Liability of Suboxone Versus Subutex
NCT01447212	PHASE3	COMPLETED	Study to Assess Longer-term Opioid Medication Effectiveness (SALOME)
NCT00000326	PHASE2	WITHDRAWN	Buprenorphine/Naloxone Treatment for Opioid Dependence-Experiment 1 - 1
NCT00000327	PHASE2	WITHDRAWN	Buprenorphine/Naloxone Treatment for Opioid Dependence-Experiment I(2) - 2
NCT01174927	PHASE1	COMPLETED	Effects of Diacetylmorphine (DAM) on Brain Function and Stress Response
NCT03976258	Not specified	COMPLETED	Effect of Heroin Use on Immune Activation and Cardiovascular Risk in HIV

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 43 clinical and 266 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).