Compound: stavudine
SMILES: O=c1n(cc(C)c([nH]1)=O)[C@@H]2O[C@H](CO)C=C2
InChIKey: XNKLLVCARDGLGL-JGVFFNPUSA-N
Synonyms: stavudine, sanilvudine, 3056-17-5, Zerit, 2',3'-Didehydro-3'-deoxythymidine, Estavudina, Stavudinum, Thymidine, 2',3'-didehydro-3'-deoxy-, Zerit Xr, BMY-27857, D 4T (nucleoside), 3'-Deoxy-2'-thymidinene, 1-((2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione, 2',3'-Didehydro-3'-deoxythimidine, 3'-Deoxy-2',3'-didehydrothymidine, BMY 27857, Stavudine (d4T), Dideoxydidehydrothymidine, BO9LE4QFZF, DTXSID1023819, 1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine, BMY27857, Stavudine (dt4), 2'-Thymidinene, 3'-deoxy-, NSC-759897, 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione, NSC-163661, DTXCID803819, 1-[(2R,5S)-5-(HYDROXYMETHYL)-2,5-DIHYDROFURAN-2-YL]-5-METHYL-1,2,3,4-TETRAHYDROPYRIMIDINE-2,4-DIONE, CHEBI:63581, NSC163661, 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione, 2',3' Didehydro 3' deoxythymidine, 2',3'-Didehydro-2',3'-dideoxythmidine, 1-((2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4-dione, 1-((2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione, Didehydrodeoxythymidine, RefChem:57733, 1-(2,3-dideoxy-beta-glycero-pent-2-enofuranosyl)thymine, Thymine, 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)-(7CI,8CI), Lion, d4T, Stavudinum [INN-Latin], Estavudina [INN-Spanish], ddeThd, MFCD00132921, Sanilvudine (JAN), D-4T, STV, CHEMBL991, Zerut XR, MLS000028546, NCGC00023212-07, SMR000058350, SANILVUDINE [JAN], NSC 163661, 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione, Stavudine [USAN:BAN:INN], 1-(2,3-Dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)thymine, D 4T, ddeTyd, 1-(cis-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione, 220020-60-0, CAS-3056-17-5, Zerit(TM), Zerit (TN), HSDB 7338, SR-01000075802, UNII-BO9LE4QFZF, Stavudine (USAN/INN), BRN 0618327, D4T & GM-CSF, Stavudine RS, Stavudine CRS, Stavudine [USAN:USP:INN:BAN], D4TMBY-27857-3, Stavudine (Standard), 1-(2,3-Dideoxy-beta-D-glycero-2-pentenofuranosyl)thymine, STAVUDINE [INN], STAVUDINE [MI], STAVUDINE [HSDB], STAVUDINE [USAN], Opera_ID_1281, STAVUDINE [MART.], D 1413, cid_5155, STAVUDINE [USP-RS], STAVUDINE [WHO-DD], STAVUDINE [WHO-IP], 3''-deoxy-2''-thymidine, Lopac0_000336, SCHEMBL38661, STAVUDINE [EMA EPAR], cid_18283, MLS000759504, MLS001055348, MLS001077292, MLS001424091, MLS006011922, BIDD:GT0082, Stavudine - Bio-X trade mark, 2',3'-Anhydrothymidine; d4T, STAVUDINE [EP IMPURITY], STAVUDINE [ORANGE BOOK], STAVUDINE [EP MONOGRAPH], GTPL12678, HY-B0116R, STAVUDINE [USP MONOGRAPH], STAVUDINUM [WHO-IP LATIN], GLXC-07997, HMS2051O20, HMS2234C10, HMS3039O05, HMS3259L21, HMS3261C13, HMS3428C07, HMS3714N22, Pharmakon1600-01502339, STAVUDINE (D4T) [VANDF], STAVUDINE (DT4) [VANDF], HY-B0116, Tox21_110886, Tox21_201393, Tox21_300583, Tox21_500336, BBL033763, BDBM50013111, EBC-07706, NSC759897, Stavudine for system suitability CRS, Stavudine(Zidovudine EP Impurity A), STK801888, Zidovudine EP Impurity A; Stavudine, AKOS005622554, Tox21_110886_1, AC-5263, CCG-100902, CS-1872, DB00649, KS-1115, LP00336, NC00152, NC00684, ND07118, SDCCGSBI-0050324.P002, ZIDOVUDINE IMPURITY A [WHO-IP], 1-((2R,5S)-5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione, 2'',3''-didehydro-3''-deoxythymidine, 3''-deoxy-2'',3''-didehydrothymidine, 3'-Deoxy-2',3'-didehydro-D-thymidine, NCGC00023212-03, NCGC00023212-04, NCGC00023212-05, NCGC00023212-08, NCGC00023212-09, NCGC00023212-10, NCGC00023212-11, NCGC00023212-12, NCGC00023212-13, NCGC00023212-14, NCGC00023212-25, NCGC00023212-30, NCGC00254372-01, NCGC00258944-01, NCGC00261021-01, Stavudine 100 microg/mL in Acetonitrile, 1-[5-(hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione & Colony-stimulating factor 2, BD164571, SMR000673569, SY057970, 2',3'-didehydro-2',3'-dideoxythymidine, Thymidine, 2',3'-didehydro-, 3'-deoxy-, ZIDOVUDINE IMPURITY A [EP IMPURITY], D3580, EU-0100336, NS00002353, 2'',3''-dideoxy-2'',3''-didehydrothymidine, C07312, D00445, EN300-120634, AB00383018_18, F404709, Q423984, SR-01000075802-1, SR-01000075802-4, 2',3'-Didehydro-3'-deoxythymidine, >=98% (TLC), BRD-K93880783-001-26-6, Z1530425068, Stavudine, European Pharmacopoeia (EP) Reference Standard, Stavudine, United States Pharmacopeia (USP) Reference Standard, Thymine, 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)-, 1-(5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione, 1-(5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (ddeThd), 3'- Azido-3'-deoxythymidine & Granulocyte-macrophage colony-stimulating factor, Stavudine for system suitability, European Pharmacopoeia (EP) Reference Standard
Theoretical properties:
molecular_formula: C10H12N2O4
molecular_weight: 224.21 g/mol
exact_mass: 224.07970687 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 16
topological_polar_surface_area: 78.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off white crystalline solid
color: White to off white crystalline solid
melting_point: 318 to 320 °F (NTP, 1992)
solubility: 50 to 100 mg/mL at 70 °F (NTP, 1992)
vapor_pressure: 9.5X10-12 mm Hg at 25 °C /Estimated/
Descriptions:
pubchem: Stavudine is a nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase. It has a role as an antiviral agent, an antimetabolite and an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor. It is an organic molecular entity, a dihydrofuran and a nucleoside analogue. It is functionally related to a thymine.
chebi: A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase
chembl: STAVUDINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Stavudine (d4T), sold under the brand name Zerit among others, is an antiretroviral medication used to prevent and treat HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needlestick injury or other potential exposure. However, it is not a first-line treatment. It is given by mouth.
Common side effects include headache, diarrhea, vomiting, rash, and peripheral nerve problems. Severe side effects include high blood lactate, pancreatitis, and an enlarged liver. It is not generally recommended in pregnancy. Stavudine is in the nucleoside analog reverse-transcriptase inhibitor (NRTI) class of medication.
Stavudine was first described in 1966 and approved for use in the United States in 1994. It is available as a generic medication.