Pingyangmycin

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]

Pingyangmycin

Clinical data
Other names	Bleomycin A5
Pregnancy category	D
Routes of administration	intravenous, intra-arterial, intramuscular, intratumoral
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	amidase
Elimination half-life	1.3 hours
Excretion	renal (25-50%)
Identifiers
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
CAS Number	11116-32-8 55658-47-4 (hydrochloride)
PubChem CID	84046
ChemSpider	8232875
UNII	5DY91Y7601
ECHA InfoCard	100.031.221
Chemical and physical data
Formula	C57H89N19O21S2
Molar mass	1440.56126 g·mol^−1
3D model (JSmol)	Interactive image
SMILES 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 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

In China, pingyangmycin has largely superseded bleomycin A₂ (commonly known as "bleomycin"), since it is more effective, costs less, is easier to get, can treat a larger variety of cancers (such as breast cancer and liver cancer) and causes less lung injury.[2][3] Though pingyangmycin and bleomycin can each cause pulmonary fibrosis, pingyangmycin's most serious side effect - which it does not share with bleomycin - 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 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.