Cefpiramide (BioDeep_00000597100)

   


代谢物信息卡片


Cefpiramide acid

化学式: C25H24N8O7S2 (612.1209314)
中文名称: 头孢吡胺
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CC(=O)C(=CN1)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
InChI: InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1

描述信息

A third-generation cephalosporin antibiotic with [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and (R)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a broad spectrum of antibacterial activity.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01D - Other beta-lactam antibacterials > J01DD - Third-generation cephalosporins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D002511 - Cephalosporins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams
C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic

同义名列表

2 个代谢物同义名

Cefpiramide acid; Cefpiramide



数据库引用编号

8 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

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文献列表

  • Jimin Yoon, Won Gun Kwack, Wang-Seob Shim, Jun Kyu Lee, Dong Kee Jang, Namyi Gu, Ji-Yoon Cho, Kyung-Tae Lee, Eun Kyoung Chung. Quantitation of plasma and biliary cefpiramide concentrations in human samples using high-performance liquid chromatography. Biomedical chromatography : BMC. 2020 Dec; 34(12):e4957. doi: 10.1002/bmc.4957. [PMID: 32706918]
  • Dean G Brown, Tricia L May-Dracka, Moriah M Gagnon, Ruben Tommasi. Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens. Journal of medicinal chemistry. 2014 Dec; 57(23):10144-61. doi: 10.1021/jm501552x. [PMID: 25402200]
  • Ken Grime, Stuart W Paine. Species differences in biliary clearance and possible relevance of hepatic uptake and efflux transporters involvement. Drug metabolism and disposition: the biological fate of chemicals. 2013 Feb; 41(2):372-8. doi: 10.1124/dmd.112.049312. [PMID: 23139379]
  • Masanori Nakakariya, Midori Ono, Nobuyuki Amano, Toshiya Moriwaki, Kazuya Maeda, Yuichi Sugiyama. In vivo biliary clearance should be predicted by intrinsic biliary clearance in sandwich-cultured hepatocytes. Drug metabolism and disposition: the biological fate of chemicals. 2012 Mar; 40(3):602-9. doi: 10.1124/dmd.111.042101. [PMID: 22190695]
  • Ji Yeon Lee, Sang-Man Jin, Chang-Hoon Lee, Byoung Jun Lee, Chang-Hyun Kang, Jae-Joon Yim, Young Tae Kim, Seok-Chul Yang, Chul-Gyu Yoo, Sung Koo Han, Joo Hyun Kim, Young Soo Shim, Young Whan Kim. Risk factors of postoperative pneumonia after lung cancer surgery. Journal of Korean medical science. 2011 Aug; 26(8):979-84. doi: 10.3346/jkms.2011.26.8.979. [PMID: 21860545]
  • Qingxue Sun, Ming Shi, Wei Shao, Yang Shi, Yanwei Xi, Guihua Huang. Tissue distribution and pulmonary targeting studies of cefpiramide sodium-loaded liposomes. Journal of drug targeting. 2011 Jan; 19(1):49-55. doi: 10.3109/10611861003667607. [PMID: 20205530]
  • Yukio Kato, Seiko Takahara, Sayaka Kato, Yoshiyuki Kubo, Yoshimichi Sai, Ikumi Tamai, Hikaru Yabuuchi, Akira Tsuji. Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jun; 36(6):1088-96. doi: 10.1124/dmd.107.019125. [PMID: 18339814]
  • Young Wan Kim, Jae Gil Lee, Kyung Sik Kim, Dong Sub Yoon, Woo Jung Lee, Byung Ro Kim, Eun Ah Shin, Young Nyun Park, Jin Sub Choi. Inflammatory pseudotumor of the liver treated by hepatic resection: a case report. Yonsei medical journal. 2006 Feb; 47(1):140-3. doi: 10.3349/ymj.2006.47.1.140. [PMID: 16502497]
  • Motoe Takayanagi, Naoyo Sano, Hajime Takikawa. Biliary excretion of olmesartan, an anigotensin II receptor antagonist, in the rat. Journal of gastroenterology and hepatology. 2005 May; 20(5):784-8. doi: 10.1111/j.1440-1746.2005.03792.x. [PMID: 15853995]
  • I Muraoka, T Hasegawa, M Nadai, L Wang, S Haghgoo, O Tagaya, T Nabeshima. Biliary and renal excretions of cefpiramide in Eisai hyperbilirubinemic rats. Antimicrobial agents and chemotherapy. 1995 Jan; 39(1):70-4. doi: 10.1128/aac.39.1.70. [PMID: 7695332]
  • F Demontes-Mainard, G Vinçon, L Labat, M Amouretti, J Necciari, G Kieffer, B Bannwarth. Cefpiramide kinetics and plasma protein binding in cholestasis. British journal of clinical pharmacology. 1994 Mar; 37(3):295-7. doi: 10.1111/j.1365-2125.1994.tb04278.x. [PMID: 8198940]
  • T Yoshida, K Honma, T Ohura, H Sugano, Y Okimoto. [The penetration of cefpiramide into the skin]. The Japanese journal of antibiotics. 1992 Oct; 45(10):1270-4. doi: NULL. [PMID: 1479678]
  • K Saionji, N Miyake, K Miyake, J Igari, I Kobayashi, Y Satoh. [Free concentration and protein binding of ceftriaxone]. The Japanese journal of antibiotics. 1992 Feb; 45(2):136-42. doi: NULL. [PMID: 1613966]
  • T Ohshima, T Hasegawa, I Johno, S Kitazawa. Protein binding of cefpiramide in the plasma of various species. The Journal of pharmacy and pharmacology. 1991 Nov; 43(11):805-6. doi: 10.1111/j.2042-7158.1991.tb03487.x. [PMID: 1686912]
  • M Kuroyama, K Kumano, F Tomonaga, T Sakai, S Mashimo. [Protein binding of various cephems in healthy subjects and patients with chronic renal failure]. Nihon Jinzo Gakkai shi. 1991 Aug; 33(8):769-77. doi: . [PMID: 1770637]
  • F Demotes-Mainard, G Vinçon, M Amouretti, F Dumas, J Necciari, G Kieffer, B Begaud. Pharmacokinetics and protein binding of cefpiramide in patients with alcoholic cirrhosis. Clinical pharmacology and therapeutics. 1991 Mar; 49(3):263-9. doi: 10.1038/clpt.1991.27. [PMID: 2007321]
  • T Yamao, S Nakayama, Y Kurosaki, T Nakayama, T Kimura. Analysis of hepatic transport of cefpiramide in rats with obstructive jaundice by using isolated hepatocytes. Pharmaceutical research. 1990 Oct; 7(10):1038-41. doi: 10.1023/a:1015991116912. [PMID: 2281033]
  • I Tamai, T Maekawa, A Tsuji. Membrane potential-dependent and carrier-mediated transport of cefpiramide, a cephalosporin antibiotic, in canalicular rat liver plasma membrane vesicles. The Journal of pharmacology and experimental therapeutics. 1990 May; 253(2):537-44. doi: NULL. [PMID: 2338647]
  • C Li, S Nakayama, Y Kurosaki, T Nakayama, T Kimura. Pharmacokinetics of cefpiramide in rats acutely intoxicated with carbon tetrachloride. Journal of pharmacobio-dynamics. 1990 Mar; 13(3):186-94. doi: 10.1248/bpb1978.13.186. [PMID: 2374088]
  • K Shindo, N Oikawa, S Chida. [Cefpiramide: antibacterial activity, pharmacokinetics, and clinical evaluation]. The Japanese journal of antibiotics. 1990 Jan; 43(1):47-62. doi: NULL. [PMID: 2348553]
  • M Koga, S Fukuda, Y Moriyama, K Takenaka, Y Iguro, Y Morishita, A Taira. [Prophylactic use of cefpiramide (CPM) in open heart surgery]. Kyobu geka. The Japanese journal of thoracic surgery. 1989 Nov; 42(12):991-4. doi: NULL. [PMID: 2593411]
  • T Nakagawa, Y Oda, A Shibukawa, H Fukuda, H Tanaka. Electrokinetic chromatography for drug analysis. Separation and determination of cefpiramide in human plasma. Chemical & pharmaceutical bulletin. 1989 Mar; 37(3):707-11. doi: 10.1248/cpb.37.707. [PMID: 2752482]
  • T Yoshida. [Penetration of antibiotics into second degree burned skin in rabbits]. [Hokkaido igaku zasshi] The Hokkaido journal of medical science. 1989 Jan; 64(1):18-30. doi: NULL. [PMID: 2722125]
  • M Ohkawa, S Tokunaga, T Sugata, M Shimamura, A Okasho, S Hirano, H Matsui. Pharmacokinetics of cefpiramide in healthy volunteers, patients with various degrees of renal dysfunction, and patients on hemodialysis. Chemotherapy. 1989; 35(6):416-22. doi: 10.1159/000238705. [PMID: 2612231]
  • T Kimura, T Yamao, S Nakayama, S Honge, T Kawakami, Y Kurosaki, T Nakayama. Pharmacokinetics of cefpiramide in rats with obstructive jaundice. Journal of pharmacobio-dynamics. 1988 Dec; 11(12):839-48. doi: 10.1248/bpb1978.11.839. [PMID: 3254982]
  • J M Brogard, F Jehl, M Adloff, J F Blickle, H Monteil. High hepatic excretion in humans of cefpiramide, a new cephalosporin. Antimicrobial agents and chemotherapy. 1988 Sep; 32(9):1360-4. doi: 10.1128/aac.32.9.1360. [PMID: 3195998]
  • K Takata, S Kawamura, I Yoshida. [Prostatic tissue levels of cefpiramide (CPM)]. Hinyokika kiyo. Acta urologica Japonica. 1988 Jun; 34(6):1105-8. doi: NULL. [PMID: 2464916]
  • T Nakagawa, Y Oda, A Shibukawa, H Tanaka. Separation and determination of cefpiramide in human plasma by electrokinetic chromatography with a micellar solution and an open tubular-fused silica capillary. Chemical & pharmaceutical bulletin. 1988 Apr; 36(4):1622-5. doi: 10.1248/cpb.36.1622. [PMID: 3416380]
  • N Okishio, M Yonezu, S Hanai, K Ishiguro, M Yanaoka, Y Naide. [Clinical studies on Suncefal (cefpiramide) concentration in prostatic tissue and bladder wall]. Hinyokika kiyo. Acta urologica Japonica. 1988 Mar; 34(3):551-4. doi: NULL. [PMID: 2455441]
  • H Matsui, T Okuda. Renal tubular mechanisms for excretion of cefpiramide (SM-1652) in association with its long-lasting pharmacokinetic properties. Journal of pharmacobio-dynamics. 1988 Feb; 11(2):67-73. doi: 10.1248/bpb1978.11.67. [PMID: 3379566]
  • H Matsui, T Okuda. Penetration of cefpiramide and cefazolin into peritoneal capsular fluid in rabbits. Antimicrobial agents and chemotherapy. 1988 Jan; 32(1):33-6. doi: 10.1128/aac.32.1.33. [PMID: 3348610]
  • J M Brogard, F Jehl, J F Blickle, J P Arnaud, H Monteil. Experimental and clinical evaluation of the biliary pharmacokinetic profile of cefpiramide, a new cephalosporin with high hepatic elimination. Drugs under experimental and clinical research. 1988; 14(8):519-27. doi: NULL. [PMID: 3248507]
  • K P Fu, N Hetzel, F J Gregory, P P Hung. Therapeutic efficacy of cefpiramide-ciprofloxacin combination in experimental Pseudomonas infections in neutropenic mice. The Journal of antimicrobial chemotherapy. 1987 Oct; 20(4):541-6. doi: 10.1093/jac/20.4.541. [PMID: 3680089]
  • J E Conte. Pharmacokinetics of cefpiramide in volunteers with normal or impaired renal function. Antimicrobial agents and chemotherapy. 1987 Oct; 31(10):1585-8. doi: 10.1128/aac.31.10.1585. [PMID: 3435107]
  • F Demotes-Mainard, G Vinçon, C Jarry, J Necciari, H Albin. Micromethod for the determination of cefpiramide in human plasma and urine by high-performance liquid chromatography using automated column switching. Journal of chromatography. 1987 Aug; 419(?):388-95. doi: 10.1016/0378-4347(87)80305-5. [PMID: 3667797]
  • J E Conte, E Zurlinden. Column liquid chromatographic determination of cefpiramide in human serum and urine. Journal of chromatography. 1987 Jul; 417(2):452-7. doi: 10.1016/0378-4347(87)80144-5. [PMID: 3654896]
  • T Ikeda, T Sakai, Y Nishimura. [Pharmacokinetics of cefpiramide concentration in lung tissues]. The Japanese journal of antibiotics. 1987 May; 40(5):946-50. doi: NULL. [PMID: 3669289]
  • P Drigues, M Labrousse, T Combes, C Mas, G Roche. [Bactericidal activity of cefpiramide on P. aeruginosa using an in vitro pharmacokinetic simulation model]. Pathologie-biologie. 1986 May; 34(5):431-5. doi: NULL. [PMID: 3095776]
  • H Sakata, K Fujita, H Yoshioka. The effect of antimicrobial agents on fecal flora of children. Antimicrobial agents and chemotherapy. 1986 Feb; 29(2):225-9. doi: 10.1128/aac.29.2.225. [PMID: 3087275]
  • A Tsuji, T Terasaki, K Takanosu, I Tamai, E Nakashima. Uptake of benzylpenicillin, cefpiramide and cefazolin by freshly prepared rat hepatocytes. Evidence for a carrier-mediated transport system. Biochemical pharmacology. 1986 Jan; 35(2):151-8. doi: 10.1016/0006-2952(86)90508-3. [PMID: 3080003]
  • K P Fu, N Hetzel, P P Hung, F J Gregory. Therapeutic efficacy of cefpiramide and cefoperazone alone and in combination with gentamicin against pseudomonal infections in neutropenic mice. Chemotherapy. 1986; 32(2):166-72. doi: 10.1159/000238409. [PMID: 3698725]
  • T Terasaki, I Tamai, K Takanosu, E Nakashima, A Tsuji. Kinetic evidence for a common transport route of benzylpenicillin and probenecid by freshly prepared hepatocytes in rats. Influence of sodium ion, organic anions, amino acids and peptides on benzylpenicillin uptake. Journal of pharmacobio-dynamics. 1986 Jan; 9(1):18-28. doi: 10.1248/bpb1978.9.18. [PMID: 3712208]
  • I Obata, F Hayashi, N Imagawa, K Ochiai, K Koike, O Morimoto, S Hachiya. [Clinical trial of cefpiramide in the gynecological field]. The Japanese journal of antibiotics. 1985 Sep; 38(9):2387-96. doi: NULL. [PMID: 4079012]
  • K Ito, M Hayasaki, K Noda, H Kondo, Y Yamada. [Fundamental and clinical studies on cefpiramide in the field of obstetrics and gynecology]. The Japanese journal of antibiotics. 1985 Aug; 38(8):2348-59. doi: NULL. [PMID: 4079008]
  • M Shintani, H Kosakai, T Takayama, A Nakanishi, I Shimamoto, M Ichijo. [Fundamental and clinical studies of cefpiramide in the field of obstetrics and gynecology]. The Japanese journal of antibiotics. 1985 Aug; 38(8):2374-8. doi: NULL. [PMID: 4079011]
  • K Hirabayashi, E Okada. [Fundamental and clinical studies on cefpiramide in the field of obstetrics and gynecology]. The Japanese journal of antibiotics. 1985 Aug; 38(8):2379-83. doi: NULL. [PMID: 3908735]
  • K P Fu, T Vince, S McCloud, F J Gregory, S T Chiang, P P Hung. Experimental efficacy and pharmacokinetic properties of cefpiramide, a new cephalosporin. Drugs under experimental and clinical research. 1985; 11(11):787-91. doi: NULL. [PMID: 3939215]
  • K Sato, S Shelton, J D Nelson. Pharmacokinetics and bacteriological efficacies of apalcillin and cefpiramide in experimental pneumococcal meningitis. Antimicrobial agents and chemotherapy. 1984 Oct; 26(4):578-9. doi: 10.1128/aac.26.4.578. [PMID: 6517548]
  • K Nakagawa, M Koyama, H Matsui, C Ikeda, K Yano, N Nakatsuru, K Yoshinaga, T Noguchi. Pharmacokinetics of cefpiramide (SM-1652) in humans. Antimicrobial agents and chemotherapy. 1984 Feb; 25(2):221-5. doi: 10.1128/aac.25.2.221. [PMID: 6712202]
  • H Wexler, W T Carter, B Harris, S M Finegold. Comparative in vitro activities of cefpiramide and apalcillin against anaerobic bacteria. Antimicrobial agents and chemotherapy. 1984 Feb; 25(2):162-4. doi: 10.1128/aac.25.2.162. [PMID: 6712200]
  • T Yamamoto, J Yasuda, M Kanao, H Okada. [Fundamental and clinical studies on cefpiramide in the field of obstetrics and gynecology]. The Japanese journal of antibiotics. 1984 Jan; 37(1):145-51. doi: NULL. [PMID: 6727033]
  • T Nishimura, K Tabuki, K Hiromatsu, T Takashima, M Takagi. [Experimental and clinical evaluation of cefpiramide in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2261-8. doi: NULL. [PMID: 6655845]
  • H Meguro, B Kim, J Mashiko, S Ohnari, M Nakajo, O Arimasu, M Hiraiwa, R Fujii. [Clinical evaluation of cefpiramide in pediatric]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2177-84. doi: NULL. [PMID: 6655838]
  • I Terashima, A Nakamura, Y Okimoto, T Kurosaki, K Himi, S Uehara. [Clinical evaluation of cefpiramide in 6 cases of infection in children]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2171-6. doi: NULL. [PMID: 6655837]
  • S Nakazawa, H Sato, K Nino, Y Hirama, A Narita, H Suzuki, S Nakazawa, H Chikaoka, K Tazoe, S Oka. [Evaluation of cefpiramide, a new cephem parenteral preparation developed in Japan, in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2160-70. doi: NULL. [PMID: 6655836]
  • N Iwai, F Mizoguchi, A Sasaki, Y Taneda, H Nakamura. [Experimental and clinical evaluation of cefpiramide in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2242-60. doi: NULL. [PMID: 6655844]
  • Y Toyonaga, Y Kurosu, M Sugita, G Kawamura, H Ida, H Mochizuki, M Hori. [Experimental and clinical evaluation of cefpiramide in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2207-27. doi: . [PMID: 6655842]
  • Y Kobayashi, T Haruta, S Kuroki, M Yamakawa, K Okura. [Clinical evaluation of cefpiramide in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2269-74. doi: NULL. [PMID: 6655846]
  • K Fujita, H Sakata, K Murono, N Mukai, H Yoshioka, S Maruyama, N Sanae, A Tsuchida, Y Suzuki. [Clinical efficacy and pharmacokinetics of cefpiramide in children]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2135-41. doi: NULL. [PMID: 6655832]
  • K Jozaki, S Iwata, Y Iwasaki, Y Sato, H Sano, R Wakabayashi, S Hayano, M Ihara, K Sunakawa, M Osano. [Experimental and clinical evaluation of cefpiramide in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2195-200. doi: NULL. [PMID: 6655840]
  • T Obara, K Kudo, A Watanabe. [Clinical experience with cefpiramide in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2142-6. doi: NULL. [PMID: 6655833]
  • T Nakashima, K Aso, Y Miyachi, A Ogawa, M Yafuso, K Kuno. [Evaluation of cefpiramide in pediatrics]. The Japanese journal of antibiotics. 1983 Aug; 36(8):2228-41. doi: NULL. [PMID: 6655843]
  • H Imasaki, Y Enjoji, H Matsui, R Kawai, S Kawamura, T Okuda. Metabolic fate of [14C]SM-1652, a new antipseudomonal cephalosporin, after parenteral administration to rats. Antimicrobial agents and chemotherapy. 1983 Jul; 24(1):42-7. doi: 10.1128/aac.24.1.42. [PMID: 6625556]
  • H Suzuki, T Yoshida, H Ozaki, H Miki, Y Shiobara. [6-week intravenous toxicity test of cefpiramide in rhesus monkeys]. The Japanese journal of antibiotics. 1983 Jun; 36(6):1411-34. doi: NULL. [PMID: 6655798]
  • H Suzuki, T Yoshida, H Ozaki, H Miki, Y Shiobara. [26-week intravenous toxicity test of cefpiramide in cynomolgus monkeys]. The Japanese journal of antibiotics. 1983 Jun; 36(6):1377-410. doi: NULL. [PMID: 6655797]
  • K Fujita, H Sakata, H Yoshioka. Diarrhoea and annihilation of faecal flora associated with cefpiramide. Lancet (London, England). 1983 Feb; 1(8321):423-4. doi: 10.1016/s0140-6736(83)91545-3. [PMID: 6130417]
  • H Matsui, K Yano, T Okuda. Pharmacokinetics of the cephalosporin SM-1652 in mice, rats, rabbits, dogs, and rhesus monkeys. Antimicrobial agents and chemotherapy. 1982 Aug; 22(2):213-7. doi: 10.1128/aac.22.2.213. [PMID: 6927282]