Pingyangmycin

Pingyangmycin

Systematic (IUPAC) name
(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
Clinical data
Pregnancy category	D
Routes of administration	intravenous, intraarterial, intramuscular, intratumoral
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Metabolism	amidase
Biological half-life	1.3 hours
Excretion	renal (25-50%)
Identifiers
CAS Number	11116-32-8 55658-47-4 (hydrochloride)
PubChem	CID 84046
ChemSpider	8232875
Synonyms	Bleomycin A5
Chemical data
Formula	C57H89N19O21S2
Molar mass	1440.56126
SMILES O=C(N)[C@@H](N)CN[C@H](c1nc(N)c(c(n1)C(=O)N[C@H](C(=O)N[C@H](C)[C@@H](O)[C@@H](C(=O)N[C@H](C(=O)NCCc2nc(cs2)c3nc(C(=O)NCCCNCCCCN)cs3)[C@H](O)C)C)[C@@H](O[C@@H]5O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]5O[C@H]4O[C@H](CO)[C@@H](O)[C@H](OC(=O)N)[C@@H]4O)c6cncn6)C)CC(=O)N
InChI 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 Key:QYOAUOAXCQAEMW-UTXKDXHTSA-N

Pingyangmycin (also known as bleomycin A₅) is an antitumor glycopeptide antibiotic belonging to the bleomycin family, which is produced by Streptomyces verticillus var. pingyangensis n.sp., a variety of Streptomyces verticillus. It was discovered in 1969 at Pingyang County of Zhejiang Province in China, and was brought into clinical use in 1978.^[1]

In China, pingyangmycin has largely superseded bleomycin A₂ (commonly known as "bleomycin"), since it is more effective, costs less, is easier to get, can treat a larger varieties of cancers (such as breast cancer and liver cancer) and causes less lung injury.^[2][3] Though it also results in pulmonary fibrosis, unlike bleomycin, its most serious side effect is anaphylactic shock, which is rare, but may happen even in a low dose, and can be fatal.^[4] In addition, it causes a higher incidence of fever than bleomycin; the occurrence of this complication in patients is between 20 and 50%.

References

1. Lin, F. T.; Li, D. D.; Yang, X. P.; Li, Q.; Xue, Y. C.; Zhen, Y. S. (1979). "Antitumor activity and preclinical pharmacologic evaluation of pingyangmycin (author's transl)". Zhonghua zhong liu za zhi \Chinese journal of oncology] 1 (3): 161–166. PMID 95444.
2. Zheng, J. W.; Yang, X. J.; Wang, Y. A.; He, Y.; Ye, W. M.; Zhang, Z. Y. (2009). "Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: An evaluation of 297 consecutive patients". Oral Oncology 45 (10): 872–876. doi:10.1016/j.oraloncology.2009.02.011. PMID 19628423.
3. Xu, H. Z.; Zhang, H. Y. (1980). "The isolation and identification of pingyangmycin (author's transl)". Yao xue xue bao = Acta pharmaceutica Sinica 15 (10): 609–614. PMID 6167140.
4. Shou, B. Q.; Mao, Z.; Zhang, S. L.; Yang, Z. (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): 572–573. PMID 19927737.