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  • 77181-69-2 , Sorivudine, 索立夫定, CAS:77181-69-2
  • 77181-69-2 , Sorivudine, 索立夫定, CAS:77181-69-2
77181-69-2 , Sorivudine, 索立夫定, CAS:77181-69-277181-69-2 , Sorivudine, 索立夫定, CAS:77181-69-2

77181-69-2 , Sorivudine, 索立夫定, CAS:77181-69-2

77181-69-2 , Sorivudine,
索立夫定,
CAS:77181-69-2
C11H13BrN2O6 / 349.13

Sorivudine, 索立夫定

Sorivudine is a nucleoside analog that is used to treat HIV. It has been shown to be effective in treating solid tumours, such as lung cancer and breast cancer. Sorivudine binds to the DNA polymerase and inhibits the synthesis of viral DNA, which prevents the virus from replicating. Sorivudine is an acyclic nucleoside phosphonate that has a prodrug form (sorivudine monophosphate). This drug is taken orally and needs to be activated by intracellular phosphorylation. Sorivudine can cause side effects such as headache, nausea, vomiting, fatigue, fever, cough, pain in joints or muscles, loss of appetite, rash or other skin reactions. These are most likely due to its effect on dextran sulfate (a sugar molecule) and calcium pantothenate (a B vitamin). These side effects are more common in patients with AIDS who have taken sorivudine.

Sorivudine is a synthetic thymidine analogue with potent antiviral activity against herpes simplex and varicella zoster viruses. Sorivudine is phosphorylated into triphosphate form within the cells; this metabolite interferes with viral DNA replication by inhibiting DNA polymerase activity without been incorporated into elongating viral DNA. Due to the dangerous effects of drug-drug interactions via its metabolite, sorivudine has been removed from the market.

Sorivudine is an organic molecular entity.

Sorivudine has been used in trials studying the treatment of Chickenpox and HIV Infections.

Title: Sorivudine

CAS Registry Number: 77181-69-2

CAS Name: 1-b-D-Arabinofuranosyl-5-[(1E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione

Additional Names: 1-b-D-arabinofuranosyl-(E)-5-(2-bromovinyl)uracil; 5-bromovinyl-araU; brovavir; BV-araU; BVAU

Manufacturers' Codes: YN-72; SQ-32756

Trademarks: Usevir (Yamasa Shoyu)

Molecular Formula: C11H13BrN2O6

Molecular Weight: 349.13

Percent Composition: C 37.84%, H 3.75%, Br 22.89%, N 8.02%, O 27.50%

Literature References: Orally active antiviral agent; inhibits viral DNA synthesis. Prepn: H. Machida, S. Sakata, EP 31128; eidem, US 4386076 (1981, 1983 both to Yamassa Shoyu); S. Sakata et al., Nucleic Acids Symp. Ser. 8, s39 (1980); R. Busson et al., ibid. 9, 49 (1981). Antiviral activity and toxicity: H. Machida, S. Sakata, Antiviral Res. 4, 135 (1984). Mechanism of action studies: T. Yokota et al., Mol. Pharmacol. 36, 312 (1989); H. Machida, Adv. Exp. Med. Biol. 278, 255 (1990). Clinical trial in herpes zoster infection: M. Niimura, ibid. 267.

Properties: mp 182° (Sakata, 1980); also reported as white crystals from ethanol, mp 195-200° (dec) (Machida, Sakata, 1983). [a]D25 +0.5° (1N NaOH). LD50 in mice (mg/kg): ~3300 i.p.; >5000 s.c.; >10000 orally (Machida, Sakata, 1984).

Melting point: mp 182° (Sakata, 1980); mp 195-200° (dec) (Machida, Sakata, 1983)

Optical Rotation: [a]D25 +0.5° (1N NaOH)

Toxicity data: LD50 in mice (mg/kg): ~3300 i.p.; >5000 s.c.; >10000 orally (Machida, Sakata, 1984)

Therap-Cat: Antiviral.

Keywords: Antiviral; Purines/Pyrimidinones.

CAS Number77181-69-2
Product NameSorivudine
IUPAC Name5-[(E)-2-bromoethenyl]-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Molecular FormulaC11H13BrN2O6
Molecular Weight349.13 g/mol
InChIInChI=1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8+,10-/m1/s1
InChI KeyGCQYYIHYQMVWLT-HQNLTJAPSA-N
SMILESC1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)C=CBr
SolubilitySoluble in DMSO
Synonyms1-beta-D-arabinofuranosyl-5-(2-bromovinyl)uracil, 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil, 5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil, brovavir, BV-ara-U, BV-araU, sorivudine
Canonical SMILESC1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)C=CBr
Isomeric SMILESC1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O)/C=C/Br


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