Cleomycin B2
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00370 |
| CAS | 76741-88-3 |
| Molecular Weight | 1437.51 |
| Molecular Formula | C56H84N20O21S2 |
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Description
It is produced by the strain of Streptomyces vericillus NK68-144. Cleomycin B2 has the same structure as the corresponding bleomycin.
Specification
| Synonyms | Bleomycinamide, N(1)-(4-((aminoiminomethyl)amino)butyl)-16-de(1-hydroxyethyl)-16-(1-hydroxycyclopropyl)-, (16S)- |
| 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-methylpyrimidine-4-carbonyl]amino]-3-[[(2R,3S,4S)-5-[[(1S)-2-[2-[4-[4-[4-(diaminomethylideneamino)butylcarbamoyl]-1,3-thiazol-2-yl]-1,3-thiazol-2-yl]ethylamino]-1-(1-hydroxycyclopropyl)-2-oxoethyl]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 |
| Canonical 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(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCCCN=C(N)N)C7(CC7)O)O |
| InChI | InChI=1S/C56H84N20O21S2/c1-20-32(73-45(76-43(20)59)24(12-30(58)79)68-13-23(57)44(60)85)48(88)74-33(39(25-14-64-19-69-25)95-53-41(37(83)35(81)28(15-77)94-53)96-52-38(84)40(97-55(63)91)36(82)29(16-78)93-52)49(89)70-22(3)34(80)21(2)46(86)75-42(56(92)7-8-56)50(90)66-11-6-31-71-27(18-98-31)51-72-26(17-99-51)47(87)65-9-4-5-10-67-54(61)62/h14,17-19,21-24,28-29,33-42,52-53,68,77-78,80-84,92H,4-13,15-16,57H2,1-3H3,(H2,58,79)(H2,60,85)(H2,63,91)(H,64,69)(H,65,87)(H,66,90)(H,70,89)(H,74,88)(H,75,86)(H2,59,73,76)(H4,61,62,67)/t21-,22+,23-,24-,28-,29+,33-,34-,35+,36+,37-,38-,39-,40-,41-,42+,52+,53-/m0/s1 |
| InChI Key | HHZSNKZXZCTAOT-BEZFEASDSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor) |
Reference Reading
1. A Novel Compound Sclerosant: Polidocanol-Bleomycin Foam
Zhang Hanshu, Liu Shaohua, Chen Anwei Dermatol Surg. 2020 Dec;46(12):1712-1714. doi: 10.1097/DSS.0000000000002533.
Background: Foam sclerotherapy is an effective treatment strategy for venous malformations. Both polidocanol (POL) and bleomycin are effective sclerosants; however, no studies have reported POL-bleomycin foam. Objective: To introduce a method for producing POL-bleomycin foam and evaluate the stability of POL-bleomycin foam with bleomycin concentrations. Materials and methods: Group A: 2 mL of 1% POL + 8 mL of air; Group B: 2 mL of 1% POL + 3 U bleomycin + 8 mL of air; Group C: 2 mL of 1% POL + 6 U bleomycin + 8 mL of air; Group D: 2 mL of 1% POL + 12 U bleomycin + 8 mL of air. Tessari method was used for foam generation. The foam half-life time (FHT) was used to evaluate foam stability. Five recordings were made for each group. Results: The FHT was 148.6 ± 2.9 seconds in Group A, 148.8 ± 4.0 seconds in Group B, 148.4 ± 2.6 seconds in Group C, and 148.8 ± 1.6 seconds in Group D. The FHT in different groups showed no significant differences. Conclusion: The POL-bleomycin foam was prepared successfully and its FHT was as long as the POL foam.
2. Bleomycin in dermatology: a review of intralesional applications
Peter Saitta, Karthik Krishnamurthy, Lance H Brown Dermatol Surg. 2008 Oct;34(10):1299-313. doi: 10.1111/j.1524-4725.2008.34281.x. Epub 2008 Jun 27.
Intralesional bleomycin has been favorably used off-label to treat various skin conditions. These include warts, hemangiomas, vascular malformations, telangiectasias, several types of cutaneous malignancies, condyloma acuminata, and the lesions of leishmaniasis cutis. Currently, there is a limited amount of evidence from randomized placebo-controlled trials comparing intralesional bleomycin with other local treatments for these disorders. In this article, we review the pharmacodynamics, mechanism of action, safety profile, and clinical applications of intralesional bleomycin. Dosages, techniques for administration, and efficacy of intralesional bleomycin for each aforementioned clinical entity are also provided. Given its ease and safety in administration, efficacy, and availability, off-label use of intralesional bleomycin can be considered another primary and/or adjunctive therapy for various common cutaneous conditions by practitioners in dermatology today.
3. Intralesional Bleomycin Injections for Vascular Malformations: A Systematic Review and Meta-Analysis
Sophie E R Horbach, Irma M Rigter, J Henk Sillevis Smitt, Jim A Reekers, Phyllis I Spuls, Chantal M A M van der Horst Plast Reconstr Surg. 2016 Jan;137(1):244-256. doi: 10.1097/PRS.0000000000001924.
Background: Vascular malformations are congenital anomalies of the vascular system. Intralesional bleomycin injections are commonly used to treat vascular malformations. However, pulmonary fibrosis could potentially be a severe complication, known from systemic bleomycin therapy for malignancies. In this study, the authors investigate the effectiveness and safety of bleomycin (A2, B2, and A5) injections for vascular malformations, when possible relative to other sclerosants. Methods: The authors performed a PubMed, Embase, Cochrane Central Register of Controlled Trials, and gray literature search for studies (1995 to the present) reporting outcome of intralesional bleomycin injections in patients with vascular malformations (n ≥ 10). Predefined outcome measures of interest were size reduction, symptom relief, quality of life, adverse events (including pulmonary fibrosis), and patient satisfaction. Results: Twenty-seven studies enrolling 1325 patients were included. Quality of evidence was generally low. Good to excellent size reduction was reported in 84 percent of lymphatic and 87 percent of venous malformations. Pulmonary fibrosis was never encountered. Meta-analysis of four studies on venous malformations treated with bleomycin versus other sclerosants showed similar size reduction (OR, 0.67; 95 percent CI, 0.24 to 1.88) but a significantly lower adverse event rate (OR, 0.1; 95 percent CI, 0.03 to 0.39) and fewer severe complications after bleomycin. Symptom relief, quality of life, and patient satisfaction were reported inadequately. Conclusions: The authors' data suggest that bleomycin is effective in reducing the size of lymphatic and venous malformations, and leads to a lower adverse event rate and fewer severe complications than other sclerosants. The included literature does not provide evidence that pulmonary fibrosis is a complication of intralesional bleomycin injections. This study represents the "best available" evidence; however, only low- to moderate-quality studies were available. Clinical question/level of evidence: Therapeutic, IV.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
