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Pingyangmycin

From Wikipedia, the free encyclopedia
Glycopeptide antibiotic used to treat various cancers
Pharmaceutical compound
Pingyangmycin
Clinical data
Other namesBleomycin A5
Pregnancy
category
  • D
Routes of
administration
intravenous, intra-arterial,intramuscular, intratumoral
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolismamidase
Eliminationhalf-life1.3 hours
Excretionrenal (25-50%)
Identifiers
  • (2R,3S,4S,5R,6R)-2-{[(2R,3S,4S,5S,6S)-2-{[(1R,2S)-2-[({6-Amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl]-5-methyl-4-pyrimidinyl}carbonyl)amino]-3-{[(2R,3S,4S)-5-{[(2S,3R)-1- ({2-[4-({3-[(4-aminobutyl)amino]propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)-3-hydroxy-1-oxo-2-butanyl]amino}-3-hydroxy-4-methyl-5-oxo-2-pentanyl]amino}-1-(1H-imidazol-5-yl)-3-oxopropyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate
CAS Number
PubChemCID
ChemSpider
UNII
ECHA InfoCard100.031.221Edit this at Wikidata
Chemical and physical data
FormulaC57H89N19O21S2
Molar mass1440.57 g·mol−1
3D model (JSmol)
  • C[C@@H](O)[C@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)c1nc(nc(N)c1C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](O[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]1O)c1c[nH]cn1)C(=O)NCCc1nc(cs1)-c1nc(cs1)C(=O)NCCCNCCCCN
  • InChI=1S/C57H89N19O21S2/c1-22-35(73-48(76-46(22)61)27(14-33(60)80)68-15-26(59)47(62)86)52(90)75-37(43(28-16-65-21-69-28)95-56-45(41(84)39(82)31(17-77)94-56)96-55-42(85)44(97-57(63)92)40(83)32(18-78)93-55)53(91)70-24(3)38(81)23(2)49(87)74-36(25(4)79)51(89)67-13-8-34-71-30(20-98-34)54-72-29(19-99-54)50(88)66-12-7-11-64-10-6-5-9-58/h16,19-21,23-27,31-32,36-45,55-56,64,68,77-79,81-85H,5-15,17-18,58-59H2,1-4H3,(H2,60,80)(H2,62,86)(H2,63,92)(H,65,69)(H,66,88)(H,67,89)(H,70,91)(H,74,87)(H,75,90)(H2,61,73,76)/t23-,24+,25+,26-,27-,31-,32+,36-,37-,38-,39+,40+,41-,42-,43-,44-,45-,55+,56-/m0/s1 checkY
  • Key:QYOAUOAXCQAEMW-UTXKDXHTSA-N checkY

Pingyangmycin (also known asbleomycin A5) is anantitumorglycopeptide antibiotic belonging to thebleomycin family, which is produced byStreptomyces verticillus var. pingyangensis n.sp., avariety ofStreptomyces verticillus. It was discovered in 1969 atPingyang County ofZhejiang Province inChina, and was brought into clinical use in 1978.[1]

In China, pingyangmycin has largely superseded bleomycin A2 (commonly known as "bleomycin"), since according to Chinese sources it is more effective, costs less, is easier to get, can treat a larger variety ofcancers (such asbreast cancer andliver cancer) and causes lesslung injury.[2][3] Though pingyangmycin and bleomycin can each causepulmonary fibrosis, pingyangmycin's most seriousside effect - which it does not share with bleomycin - isanaphylactic shock, which is rare, but may happen even in a low dose, and can be fatal.[4] In addition, it causes a higher incidence offever than bleomycin; the occurrence of this complication in patients is between 20 and 50%.

References

[edit]
  1. ^Lin FT, Li DD, Yang XP, Li Q, Xue YC, Zhen YS (1979). "[Antitumor activity and preclinical pharmacologic evaluation of pingyangmycin (author's transl)]".Zhonghua Zhong Liu Za Zhi [Chinese Journal of Oncology].1 (3):161–6.PMID 95444.
  2. ^Zheng JW, Yang XJ, Wang YA, He Y, Ye WM, Zhang ZY (October 2009). "Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: an evaluation of 297 consecutive patients".Oral Oncology.45 (10):872–6.doi:10.1016/j.oraloncology.2009.02.011.PMID 19628423.
  3. ^Xu HZ, Zhang HY (October 1980). "[The isolation and identification of pingyangmycin (author's transl)]".Yao Xue Xue Bao = Acta Pharmaceutica Sinica.15 (10):609–14.PMID 6167140.
  4. ^Shou BQ, Mao Z, Zhang SL, Yang Z (October 2009). "[Allergy caused by minidose and low concentration Pingyangmycin: a case report]".Hua Xi Kou Qiang Yi Xue Za Zhi = Huaxi Kouqiang Yixue Zazhi = West China Journal of Stomatology.27 (5):572–3.PMID 19927737.
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