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			{{Short description\|Glycopeptide antibiotic used to treat various cancers}}
	{{Drugbox		{{Drugbox
	\| IUPAC_name = <nowiki>-3-oxopropyl]-5-~~methylpyrimidine~~-4-carbonyl]amino]-3--1,3-~~thiazol-2-yl]~~-1,3-thiazol-2-yl]~~ethylamino]~~-3-hydroxy-1-~~oxobutan~~-2-yl]amino]-3-hydroxy-4-methyl-5-~~oxopentan~~-2-yl]amino]-1-(1H-imidazol-5-yl)-3-~~oxopropoxy~~]-4,5-dihydroxy-6-(hydroxymethyl)~~oxan~~-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)~~oxan~~-4-yl] carbamate~~</nowiki>~~		\| IUPAC_name = (2''R'',3''S'',4''S'',5''R'',6''R'')-2-<nowiki/>{amino}-3-oxopropyl]-5-methyl-4-pyrimidinyl}carbonyl)amino]-3-<nowiki/>{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-(1''H''-imidazol-5-yl)-3-oxopropyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2''H''-pyran-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2''H''-pyran-4-yl carbamate
	\|image = Pingyangmycin.svg		\| image = Pingyangmycin.svg
	\| width = 300		\| width = 300

	<!--Clinical data-->		<!--Clinical data-->
	\| pregnancy_category = D		\| pregnancy_category = D
	\| legal_status = Rx-only		\| legal_status = Rx-only
	\| routes_of_administration = ], ~~intraarterial~~, ], intratumoral		\| routes_of_administration = ], intra-arterial, ], intratumoral

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	\| metabolism = ]		\| metabolism = ]
	\| elimination_half-life = 1.3 hours		\| elimination_half-life = 1.3 hours
	\| excretion = ] (25-50%)		\| excretion = ] (25-50%)

	<!--Identifiers-->		<!--Identifiers-->
	\| ~~CASNo_Ref~~ = {{cascite\|correct\|CAS}}		\| CAS_number_Ref = {{cascite\|correct\|CAS}}
	\| CAS_number = 11116-32-8		\| CAS_number = 11116-32-8
	\| CAS_supplemental = <br/>{{CAS\|55658-47-4\|(hydrochloride)}}		\| CAS_supplemental = <br/>{{CAS\|55658-47-4\|(hydrochloride)}}
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 5DY91Y7601
	\| PubChem = 84046		\| PubChem = 84046
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = ~~75831~~		\| ChemSpiderID = 8232875
			\| synonyms = Bleomycin A5

	<!--Chemical data-->		<!--Chemical data-->
	\| C=57 \| H=89 \| N=19 \| O=21 \| S=2		\| C=57 \| H=89 \| N=19 \| O=21 \| S=2
			\| smiles = C(O)(NC(=O)(C)(O)(C)NC(=O)(NC(=O)c1nc(nc(N)c1C)(CC(N)=O)NC(N)C(N)=O)(O1O(CO)(O)(O)1O1O(CO)(O)(OC(N)=O)1O)c1ccn1)C(=O)NCCc1nc(cs1)-c1nc(cs1)C(=O)NCCCNCCCCN
	\| molecular_weight = 1440.56126
	\| smiles = CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)OC3C(C(C(C(O3)CO)O)O)OC4C(C(C(C(O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCCNCCCCN)O
	\| 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)
	\| InChIKey = QYOAUOAXCQAEMW-UHFFFAOYSA-N
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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)		\| StdInChI =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
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = QYOAUOAXCQAEMW-~~UHFFFAOYSA~~-N		\| StdInChIKey = QYOAUOAXCQAEMW-UTXKDXHTSA-N
	}}		}}

	'''Pingyangmycin''' (also known as '''~~Bleomycin~~ A<sub>5</sub>''') is an ] ] ~~belongs~~ to ], which is produced by ''Streptomyces verticillus var. pingyangensis n.sp.'', a ] of '']''. It was discovered in 1969 at ] of ] in ], and was brought into clinical use in 1978.<ref>{{~~Cite~~ journal \| ~~last1~~ = Lin ~~\| first1 = F. T. \| last2 =~~ Li ~~\| first2 = D. D. \| last3 =~~ Yang ~~\| first3 = X. P. \| last4 =~~ Li ~~\| first4 =~~ Q~~. \| last5 =~~ Xue ~~\| first5 = Y. C. \| last6 =~~ Zhen ~~\| first6 = Y. S.~~ \| title = Antitumor activity and preclinical pharmacologic evaluation of pingyangmycin (author's transl) \| journal = Zhonghua ~~zhong~~ ~~liu~~ za ~~zhi~~ ~~\~~Chinese ~~journal~~ of ~~oncology]~~ \| volume = 1 \| issue = 3 \| pages = ~~161–166~~ \| year = 1979 \| pmid = 95444}}</ref>		'''Pingyangmycin''' (also known as '''bleomycin A<sub>5</sub>''') is an ] ] belonging to the ] family, which is produced by ''Streptomyces verticillus'' var.'' pingyangensis n.sp.'', a ] of '']''. It was discovered in 1969 at ] of ] in ], and was brought into clinical use in 1978.<ref>{{cite journal \| vauthors = Lin FT, Li DD, Yang XP, Li Q, Xue YC, Zhen YS \| title = \| journal = Zhonghua Zhong Liu Za Zhi \| volume = 1 \| issue = 3 \| pages = 161–6 \| year = 1979 \| pmid = 95444 }}</ref>

	In China pingyangmycin has largely superseded bleomycin A<sub>2</sub> (commonly known as "bleomycin"), since it's more effective, ~~cost~~ less, easier to get, can treat a larger ~~varities~~ of ]s (such as ] and ]) and ~~cause~~ less ] injury.<ref>{{~~Cite~~ journal \| ~~last1~~ = Zheng ~~\| first1 = J. W. \| last2 =~~ Yang ~~\| first2 = X. J. \| last3 =~~ Wang ~~\| first3 = Y. A. \| last4 =~~ He ~~\| first4 =~~ Y~~. \| last5 =~~ Ye ~~\| first5 = W. M. \| last6 =~~ Zhang ~~\| first6 = Z. Y. \| doi = 10.1016/j.oraloncology.2009.02.011~~ \| title = Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: An evaluation of 297 consecutive patients \| journal = Oral Oncology \| volume = 45 \| issue = 10 \| pages = ~~872–876~~ \| ~~year~~ = 2009 \| pmid = 19628423\| ~~pmc~~ = }}</ref><ref>{{~~Cite~~ journal \| ~~last1~~ = Xu ~~\| first1 = H. Z. \| last2 =~~ Zhang ~~\| first2 = H. Y.~~ \| title = The isolation and identification of pingyangmycin (author's transl) \| journal = Yao ~~xue~~ ~~xue~~ ~~bao~~ = Acta ~~pharmaceutica~~ Sinica \| volume = 15 \| issue = 10 \| pages = ~~609–614~~ \| ~~year~~ = 1980 \| pmid = 6167140}}</ref> ~~Even~~ ~~though~~ it ~~also~~ ~~result~~ in ], ~~unlike bleomycin, it~~'s most serious ] is ], which is rare but may happen even in a low dose, and can be fatal.<ref>{{~~Cite~~ journal \| ~~last1~~ = Shou ~~\| first1 = B. Q. \| last2 =~~ Mao ~~\| first2 =~~ Z~~. \| last3 =~~ Zhang ~~\| first3 = S. L. \| last4 =~~ Yang ~~\| first4 =~~ Z. \| title = Allergy caused by minidose and low concentration Pingyangmycin: A case report \| journal = Hua xi ~~kou~~ ~~qiang~~ yi ~~xue~~ za ~~zhi~~ = Huaxi ~~kouqiang~~ ~~yixue~~ ~~zazhi~~ = West China ~~journal~~ of ~~stomatology~~ \| volume = 27 \| issue = 5 \| pages = ~~572–573~~ \| ~~year~~ = 2009 \| pmid = 19927737}}</ref> ~~Besides~~, it causes ~~more~~ ] than bleomycin: the occurrence of this complication in patients is between 20% and 50%.		In China, pingyangmycin has largely superseded bleomycin A<sub>2</sub> (commonly known as "bleomycin"), since according to Chinese sources it is more effective, costs less, is easier to get, can treat a larger variety of ]s (such as ] and ]) and causes less ] injury.<ref>{{cite journal \| vauthors = Zheng JW, Yang XJ, Wang YA, He Y, Ye WM, Zhang ZY \| title = Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: an evaluation of 297 consecutive patients \| journal = Oral Oncology \| volume = 45 \| issue = 10 \| pages = 872–6 \| date = October 2009 \| pmid = 19628423 \| doi = 10.1016/j.oraloncology.2009.02.011 }}</ref><ref>{{cite journal \| vauthors = Xu HZ, Zhang HY \| title = \| journal = Yao Xue Xue Bao = Acta Pharmaceutica Sinica \| volume = 15 \| issue = 10 \| pages = 609–14 \| date = October 1980 \| pmid = 6167140 }}</ref> Though pingyangmycin and bleomycin can each cause ], pingyangmycin's most serious ] - which it does not share with bleomycin - is ], which is rare, but may happen even in a low dose, and can be fatal.<ref>{{cite journal \| vauthors = Shou BQ, Mao Z, Zhang SL, Yang Z \| title = \| journal = Hua Xi Kou Qiang Yi Xue Za Zhi = Huaxi Kouqiang Yixue Zazhi = West China Journal of Stomatology \| volume = 27 \| issue = 5 \| pages = 572–3 \| date = October 2009 \| pmid = 19927737 }}</ref> In addition, it causes a higher incidence of ] than bleomycin; the occurrence of this complication in patients is between 20 and 50%.

	==References==		== References ==
	{{reflist}}		{{reflist}}

	]		]
	]		]
	]

	]

Latest revision as of 04:22, 25 March 2024

Glycopeptide antibiotic used to treat various cancers Pharmaceutical compound

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-{amino}-3-oxopropyl]-5-methyl-4-pyrimidinyl}carbonyl)amino]-3-{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	1440.57 g·mol
3D model (JSmol)	Interactive image
SMILES C(O)(NC(=O)(C)(O)(C)NC(=O)(NC(=O)c1nc(nc(N)c1C)(CC(N)=O)NC(N)C(N)=O)(O1O(CO)(O)(O)1O1O(CO)(O)(OC(N)=O)1O)c1ccn1)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

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.

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 of cancers (such as breast cancer and liver cancer) and causes less lung injury. 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. In addition, it causes a higher incidence of fever than bleomycin; the occurrence of this complication in patients is between 20 and 50%.

References

Lin FT, Li DD, Yang XP, Li Q, Xue YC, Zhen YS (1979). "". Zhonghua Zhong Liu Za Zhi . 1 (3): 161–6. PMID 95444.
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.
Xu HZ, Zhang HY (October 1980). "". Yao Xue Xue Bao = Acta Pharmaceutica Sinica. 15 (10): 609–14. PMID 6167140.
Shou BQ, Mao Z, Zhang SL, Yang Z (October 2009). "". 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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