abacavir

CHEBI:421707 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:38001 CHEBI:38001

Chemical structure

Computed structure properties
Molecular formula	C14H18N6O
Charge	0
Average mass	286.339 Da
Monoisotopic mass	286.15421 Da
Source	ChEBI
InChIKey	MCGSCOLBFJQGHM-SCZZXKLOSA-N

SMILES

Nc1nc(NC2CC2)c2ncn([C@H]3C=C[C@@H](CO)C3)c2n1

InChI

InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1

Also called

{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol (EXACT_SYNONYM)— chebi
ABC (EXACT_SYNONYM)— chebi
Abacavir (EXACT_SYNONYM)— chebi
{(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

beilstein:7493116
cas:136470-78-5
drugbank:DB01048
drugcentral:34
kegg.compound:C07624
kegg.drug:D07057
reaxys:7493116
wikipedia.en:Abacavir

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:36044 CHEBI:36044
CHEBI:53756 CHEBI:53756

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:421707`	abacavir	`antibioticmech:chebi-26e5f8eb51`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.