delavirdine
CHEBI:119573
·resolve ·ANTIVIRAL
·EXACT
SEEDED
The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for 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.
Chemical structure
Computed structure properties
| Molecular formula | C22H28N6O3S |
|---|
| Charge | 0 |
|---|
| Average mass | 456.572 Da |
|---|
| Monoisotopic mass | 456.19436 Da |
|---|
| Source | ChEBI |
|---|
| InChIKey | WHBIGIKBNXZKFE-UHFFFAOYSA-N |
|---|
SMILES
CC(C)Nc1cccnc1N1CCN(C(=O)c2cc3cc(NS(C)(=O)=O)ccc3n2)CC1
InChI
InChI=1S/C22H28N6O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26H,9-12H2,1-3H3
Also called
- N-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1H-indol-5-yl]methanesulfonamide (EXACT_SYNONYM)— chebi
- (N-[2-[4-[3-(1-methylethylamino)pyridin-2-yl]piperazin-1-yl]carbonyl-1H-indol-5-yl] methanesulfonamide) (EXACT_SYNONYM)— chebi
- 1-(3-((1-methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1H-indol-2-yl)carbonyl)piperazine (EXACT_SYNONYM)— chebi
- 2-(4-(5-methanesulfonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamine (EXACT_SYNONYM)— chebi
- Delavirdine (EXACT_SYNONYM)— chebi
- N-(2-(1-(3-(isopropylamino)pyridin-2-yl)piperazine-4-carbonyl)-1H-indol-5-yl)methanesulfonamide (EXACT_SYNONYM)— chebi
- N-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yl}-methanesulfonamide (EXACT_SYNONYM)— chebi
Cross-references
Equivalent identifiers for this same structure in other resources.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
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:119573 |
delavirdine |
antibioticmech:chebi-10f5984ad7 |
2026-08-30 |
Molecular targets
The molecular entity or process this compound acts on. Each target
carries evidence — this is a mechanistic claim, not a classification.
Gag-Pol polyprotein [588-1027,K690N]/[588-1147,K690N] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Human immunodeficiency virus 1 NCBITaxon:11676
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| IC50 |
625 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 3490
assay 457_1
monomer 1944 |
PMID:10514285 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Gag-Pol polyprotein UniProtKB:P04585 |
— |
Human immunodeficiency virus 1 |
REVIEWED |
- PMID:10514285 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Gag-Pol polyprotein [588-1027,P823L]/[588-1147,P823L] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Human immunodeficiency virus 1 NCBITaxon:11676
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| IC50 |
18000 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 3262
assay 402_1
monomer 1944 |
PMID:8809165 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Gag-Pol polyprotein UniProtKB:P04585 |
— |
Human immunodeficiency virus 1 |
REVIEWED |
- PMID:8809165 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Gag-Pol polyprotein [588-1027]/[588-1147] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Human immunodeficiency virus 1 NCBITaxon:11676
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| IC50 |
260 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 2135
assay 402_1
monomer 1944 |
PMID:8809165 |
| IC50 |
1100 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 2808
assay 427_1
monomer 1944 |
PMID:7684450 |
| IC50 |
1100 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 2952
assay 5_1
monomer 1944 |
PMID:10698447 |
| IC50 |
1.3 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 3474
assay 457_1
monomer 1944 |
PMID:10514285 |
| IC50 |
422 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 3664
assay 467_1
monomer 1944 |
PMID:10821714 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Gag-Pol polyprotein UniProtKB:P04585 |
— |
Human immunodeficiency virus 1 |
REVIEWED |
- PMID:8809165 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
- PMID:7684450 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
- PMID:10698447 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
- PMID:10514285 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
- PMID:10821714 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Gag-Pol polyprotein [588-1127,Y768C]/[588-1147,Y768C] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Human immunodeficiency virus 1 NCBITaxon:11676
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| IC50 |
8320 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 3277
assay 402_1
monomer 1944 |
PMID:8809165 |
| IC50 |
114 nM |
HIV-1 RT Assay
The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro. |
RSID 3482
assay 457_1
monomer 1944 |
PMID:10514285 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Gag-Pol polyprotein UniProtKB:P04585 |
— |
Human immunodeficiency virus 1 |
REVIEWED |
- PMID:8809165 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
- PMID:10514285 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
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.
Causal graphs
Evidence-backed mechanism graphs: how the compound reaches its
target, what the target does, and how the effect propagates to growth inhibition
or death.
Delavirdine inhibits HIV-1 reverse transcriptase MECHANISTIC
Delavirdine inhibits HIV-1 reverse transcriptase RNA-directed DNA polymerase activity, blocking the viral DNA synthesis step required for HIV-1 reverse transcription.
Nodes — delavirdine_hiv1_reverse_transcriptase_inhibition
| Node | Label | Type | Grounding |
|---|
delavirdine |
delavirdine |
COMPOUND |
CHEBI:119573 |
hiv1_reverse_transcriptase |
HIV-1 reverse transcriptase |
GENE_OR_PROTEIN |
REVIEWED_LABEL_ONLY |
rna_directed_dna_polymerase_activity |
RNA-directed DNA polymerase activity |
MOLECULAR_FUNCTION |
GO:0003964 |
hiv1_reverse_transcription |
HIV-1 reverse transcription |
BIOLOGICAL_PROCESS |
REVIEWED_LABEL_ONLY |
Edges — delavirdine_hiv1_reverse_transcriptase_inhibition
| Subject | Predicate | Object | Evidence |
|---|
delavirdine |
inhibits |
hiv1_reverse_transcriptase |
- PMID:8809165 (BindingDB-curated HIV-1 reverse transcriptase IC50 measurements in this record support direct inhibition by delavirdine.)
- PMID:10514285 (BindingDB-curated assays in this record measured delavirdine inhibition of wild-type and mutant HIV-1 reverse transcriptases.)
|
hiv1_reverse_transcriptase |
enables |
rna_directed_dna_polymerase_activity |
- PMID:1377403 (The first HIV-1 reverse transcriptase-inhibitor crystal structure supports reverse transcriptase as a viral DNA polymerase drug target.)
|
rna_directed_dna_polymerase_activity |
is required for |
hiv1_reverse_transcription |
- PMID:1377403 (HIV-1 reverse transcriptase structural work connects the drug target to the viral DNA polymerase activity required during reverse transcription.)
|
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
-
RESEEDED_FROM_SOURCES
2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
CURATED_CAUSAL_GRAPH
2026-09-04 · codex · LLM-assisted
Added a PMID-supported causal graph for delavirdine inhibition of HIV-1 reverse transcriptase.
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.