AntibioticMech

penciclovir

CHEBI:7956 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topically for treatment of herpes labialis. A prodrug, famciclovir, is used for oral administration. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:20702 CHEBI:20702
• CHEBI:26287 CHEBI:26287

Chemical structure

Computed structure properties

Molecular formula	C10H15N5O3
Charge	0
Average mass	253.262 Da
Monoisotopic mass	253.11749 Da
Source	ChEBI
InChIKey	JNTOCHDNEULJHD-UHFFFAOYSA-N

SMILES

Nc1nc(=O)c2ncn(CCC(CO)CO)c2n1

InChI

InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17/h5-6,16-17H,1-4H2,(H3,11,13,14,18)

Also called

• penciclovirum (INN)— chebi
• 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one (EXACT_SYNONYM)— chebi
• 9-(4-hydroxy-3-(hydroxymethyl)butyl)guanine (EXACT_SYNONYM)— chebi
• 9-(4-hydroxy-3-hydroxymethylbut-1-yl)-guanine (EXACT_SYNONYM)— chebi
• 9-[2-hydroxy-1-(hydroxymethyl)-ethoxymethyl]guanine (EXACT_SYNONYM)— chebi
• 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine (EXACT_SYNONYM)— chebi
• PCV (EXACT_SYNONYM)— chebi
• PE2 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:39809-25-1
• drugbank:DB00299
• drugcentral:2079
• hmdb:HMDB0014444
• kegg.compound:C07417
• kegg.drug:D05407
• lincs.smallmolecule:LSM-5587
• patent:US5075445
• pdb-ccd:PE2
• reaxys:4501039
• wikipedia.en:Penciclovir

Activity roles

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

• CHEBI:36044 CHEBI:36044

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:7956	penciclovir	antibioticmech:chebi-d2299e6784	2026-08-30

Mechanism summary

Clinical status

APPROVED

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · 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.