Compound: acyclovir
SMILES: O=c1nc([nH]c2c1ncn2COCCO)N
InChIKey: MKUXAQIIEYXACX-UHFFFAOYSA-N
Synonyms: acyclovir, 59277-89-3, Aciclovir, Acycloguanosine, 9-[(2-Hydroxyethoxy)methyl]guanine, Virorax, Vipral, Wellcome-248U, Aciclovirum, Sitavig, Acicloftal, Gerpevir, Aciclovirum [Latin], Cargosil, Novirus, BW-248U, 9-((2-Hydroxyethoxy)methyl)guanine, 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one, CHEBI:2453, Cyclovir, 2-Amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-6H-purin-6-one, 2-Amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one, 2-Amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one, X4HES1O11F, NSC-645011, NSC-758477, AVACLYR, DTXSID1022556, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-, NSC645011, 9-[(2-Hydroxyethoxy)-methyl]guanine, DTXCID102556, 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-, Aciclovirum (Latin), 2-amino-9-((2-hydroxyethoxy)methyl)-1,9-dihydro-6H-purin-6-one, 9-((2-Hydroxyethoxy)-methyl)guanine, Aclovir, Clearsore, Duvimex, Lipsore, Ranovir, Soothelip, Soraway, Viralief, Virasorb, Lypsyl, Avert, ViraxPuren, Cymex ultra, 2-amino-9-((2-hydroxyethoxy)methyl)-6,9-dihydro-3H-purin-6-one, Aci Sanorania, Virax Puren, aciclovir von ct, Solutab, Acipen, Acyclo V, Alonga, Aciclovir, Sodium, Acyclovir, Aciclovir Sanorania, Aciclovir-Sanorania, Wellcome248U, Acyclovir suspension, Wellcome 248U, Virovir 200, Virovir 400, Virovir 800, RefChem:5516, D06BB03, J05AB01, S01AD03, NSC335752, 261-685-1, Zovirax, Zovir, 2-Amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one, Zyclir, 9-(2-Hydroxyethoxy)methylguanine, 9-HYROXYETHOXYMETHYLGUANINE, C8H11N5O3, W-248-U, 2-amino-9-(2-hydroxyethoxymethyl)-3H-purin-6-one, MFCD00057880, Aciclovir [INN], NSC 645011, Acyclovir-side chain-2-3H, Acyclovir (Aciclovir), ACYCLOVIR-SIDECHAIN-2-3H, 9-(2-Hydroxyethoxymethyl)guanine, Zovirax (TN), MLS000069633, AC2, Acyclovir [USAN], NCGC00015061-02, Aciclovier, Activir, Hascovir, SMR000058225, 2-amino-9-[(2-hydroxyethoxy)methyl]-3,9-dihydro-6H-purin-6-one, Aciclovir for impurity G identification CRS, CAS-59277-89-3, 6H-Purin-6-one, 1,9-dihydro-2-amino-9-((2-hydroxyethoxy)methyl)-, Aciclovirum [INN-Latin], 2-amino-9-[(2-hydroxyethoxy)methyl]hydropurin-6-one, 2-amino-9-((2-hydroxyethoxy)methyl)-3H-purin-6(9H)-one, Viropump, AcycloFoam, Genvir, Maynar, Acyclovir Lauriad, DRG-0008, Acyclovir (USP), BW 248U, CCRIS 1953, HSDB 6511, SR-01000075540, Acyclovir [USAN:USP], EINECS 261-685-1, ACV & Pluronic F-68, B-LF& ACV, UNII-X4HES1O11F, Valaciclovir EP Impurity B, Acyclovir & Pluronic F-68, Poviral, Sitavir, Acic, Cycloviran;, Supraviran;, Acycloguanosine;, Acyclovir;, Soothelip;, Herpetad;, Virasorb;, Activir;, Milavir;, Mirolex;, Virovir;, Zovirax;, Aciclovir CRS, Avirax;, Geavir;, Acyclo-V, Prestwick_6, 1pwy, BW-248-U, Sitavig (TN), Acyclovir (Standard), Spectrum_001739, ACICLOVIR [JAN], ACYCLOVIR [MI], ACICLOVIR [IARC], ACYCLOVIR [HSDB], Opera_ID_1674, Prestwick0_000086, Prestwick1_000086, Prestwick2_000086, Prestwick3_000086, Spectrum2_001563, Spectrum3_001874, Spectrum4_000225, Spectrum5_001093, ACYCLOVIR [VANDF], Lopac-A-4669, Aciclovir (JP18/INN), 2-amino-9-(2-hydroxyethoxymethyl)purin-6-ol, ACICLOVIR [MART.], CHEMBL184, Epitope ID:422870, A 4669, ACICLOVIR [WHO-DD], ACICLOVIR [WHO-IP], ACYCLOVIR [USP-RS], SCHEMBL3175, Lopac0_000037, SCHEMBL40723, ACICLOVIRUM [WHO-IP], BSPBio_000012, BSPBio_003348, KBioGR_000889, KBioSS_002219, BIDD:GT0646, DivK1c_000185, SPECTRUM1503603, SPBio_001466, SPBio_001951, 2-amino-9-[(2-hydroxyethoxy)methyl]-9H-purin-6-ol, BPBio1_000014, GTPL4829, orb1308575, SCHEMBL9828560, 9(2-hydroxyethoxymethyl)guanine, ACICLOVIR (BW 248U), ACYCLOVIR [ORANGE BOOK], ACICLOVIR [EP MONOGRAPH], HMS500J07, KBio1_000185, KBio2_002219, KBio2_004787, KBio2_007355, KBio3_002850, ACYCLOVIR [USP MONOGRAPH], NINDS_000185, GLXC-04946, HMS1568A14, HMS1922E08, HMS2090G09, HMS2095A14, HMS2234K21, HMS3259N10, HMS3260G15, HMS3269M15, HMS3372K02, HMS3413D21, HMS3655C14, HMS3677D21, HMS3712A14, HMS5080M09, Pharmakon1600-01503603, 9-(2- Hydroxyethoxymethyl)guanine, Aciclovir for peak identification 2, MSK10025, 9-(2-hydroxyethoxy methyl) guanine, Tox21_110075, Tox21_500037, 2-amino-9-{[(2-hydroxyethyl)oxy]methyl}-1,9-dihydro-6H-purin-6-one, BBL009642, BDBM50021776, BDBM50103518, CCG-39909, EBC-06676, EBC-11172, HY-17422R, NSC758477, NSC780378, s1807, SBB063281, STK796771, STL257059, STL301862, AKOS000656213, AKOS015995680, AKOS022135433, Tox21_110075_1, AC-8068, CS-1353, DB00787, IA58279, KS-1027, LP00037, NC00717, NSC-780378, SDCCGSBI-0050026.P003, Bovine lactoferrin & 2-Amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one, IDI1_000185, SMP1_000007, NCGC00015061-01, NCGC00015061-03, NCGC00015061-04, NCGC00015061-05, NCGC00015061-06, NCGC00015061-07, NCGC00015061-08, NCGC00015061-09, NCGC00015061-10, NCGC00015061-12, NCGC00015061-13, NCGC00015061-28, NCGC00015061-29, NCGC00022426-03, NCGC00093555-01, NCGC00093555-02, NCGC00093555-03, NCGC00093555-04, NCGC00167756-01, NCGC00167756-02, NCGC00260722-01, NCGC00381719-03, HY-17422, ST024744, SY051130, Acycloguanosine, >=99% (HPLC), powder, Aciclovir 1.0 mg/ml in Dimethyl Sulfoxide, 59277-89-3(API), A1915, EU-0100037, NS00009000, SW196324-3, C06810, D00222, EN300-123010, Valaciclovir hydrochloride anhydrous impurity B, F076300, Q147101, SR-01000075540-1, SR-01000075540-3, SR-01000075540-5, BRD-K32318651-001-17-9, BRD-K32318651-001-21-1, BRD-K32318651-001-22-9, BRD-K32318651-001-23-7, BRD-K32318651-001-24-5, Aciclovir, British Pharmacopoeia (BP) Reference Standard, F2173-0946, Z1546610471, Aciclovir, European Pharmacopoeia (EP) Reference Standard, VALACICLOVIR HYDROCHLORIDE IMPURITY B [EP IMPURITY], 2-Amino-9-(2-hydroxy-ethoxymethyl)-5,9-dihydro-purin-6-one, Acyclovir, United States Pharmacopeia (USP) Reference Standard, 2-Amino-1 ,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one, 2-Amino-9-(2-hydroxy-ethoxymethyl)-5,9-dihydro-purin-6-one (ACV), 2-Amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one #, 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one, VALACICLOVIR HYDROCHLORIDE HYDRATE IMPURITY B [EP IMPURITY], Acyclovir, Pharmaceutical Secondary Standard; Certified Reference Material, Aciclovir for peak identification 1, European Pharmacopoeia (EP) Reference Standard, Aciclovir for peak identification 2, European Pharmacopoeia (EP) Reference Standard, Aciclovir for system suitability, European Pharmacopoeia (EP) Reference Standard, InChI=1/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15
Theoretical properties:
molecular_formula: C8H11N5O3
molecular_weight: 225.20 g/mol
exact_mass: 225.08618923 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 4
heavy_atom_count: 16
topological_polar_surface_area: 115 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from methanol
color: Crystals from methanol
solubility: 1.41mg/mL at 25°C
Descriptions:
pubchem: Acyclovir is an oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections. It has a role as an antimetabolite and an antiviral drug. It is a member of 2-aminopurines and an oxopurine. It is functionally related to a guanine.
chebi: An oxopurine that is  guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.
chembl: ACYCLOVIR is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Aciclovir, also known as acyclovir, is an antiviral medication. It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles. Other uses include the prevention of cytomegalovirus infections following transplant, and severe complications of Epstein–Barr virus infection. It can be taken by mouth, applied as a cream, or injected.
Common side effects include nausea and diarrhea. Potentially serious side effects include kidney problems and low platelets. Greater care is recommended in those with poor liver or kidney function. It is generally considered safe for use in pregnancy with no harm having been observed. It appears to be safe during breastfeeding. Aciclovir is a nucleoside analogue that mimics guanosine. It works by decreasing the production of the virus's DNA.
Aciclovir was patented in 1974, by Burroughs Wellcome, and approved for medical use in 1981. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication and is marketed under many brand names worldwide. In 2023, it was the 150th most commonly prescribed medication in the United States, with more than 3 million prescriptions.