N-Acetyl-Calicheamicin - CAS 108212-76-6

N-Acetyl-Calicheamicin - CAS 108212-76-6 Catalog number: BADC-00723

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N-Acetyl-Calicheamicin is a potent enediyne antitumor antibiotic that could be a potential cytotoxic DNA-binding agent in antibody-drug-conjugation (ADC). Calicheamicin is a naturally occurring hydrophobic enediyne antibiotic that was isolated from the actinomycete Micromonospora echinospora calichensis.

Category
ADCs Cytotoxin
Product Name
N-Acetyl-Calicheamicin
CAS
108212-76-6
Catalog Number
BADC-00723
Molecular Formula
C57H76IN3O22S4
Molecular Weight
1410.38
Target
DNA
N-Acetyl-Calicheamicin

Ordering Information

Catalog Number Size Price Quantity
BADC-00723 1 mg $1999
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Description
N-Acetyl-Calicheamicin is a potent enediyne antitumor antibiotic that could be a potential cytotoxic DNA-binding agent in antibody-drug-conjugation (ADC). Calicheamicin is a naturally occurring hydrophobic enediyne antibiotic that was isolated from the actinomycete Micromonospora echinospora calichensis.
Synonyms
N-Acetyl-Calicheamicin γ1; N-Acetyl-Calicheamicin γ; N-Acetyl-Calicheamicin; N-Acetyl-γ-calicheamicin
IUPAC Name
S-[(2R,3S,4S,6S)-6-[[(2R,3S,4S,5R,6R)-5-[(2S,4S,5S)-5-[acetyl(ethyl)amino]-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[(2S,5Z,9R,13E)-9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate
Canonical SMILES
CCN(C1COC(CC1OC)OC2C(C(C(OC2OC3C#CC=CC#CC4(CC(=O)C(=C3C4=CCSSSC)NC(=O)OC)O)C)NOC5CC(C(C(O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)OC7C(C(C(C(O7)C)O)OC)O)I)C)O)O)C(=O)C
InChI
InChI=1S/C57H76IN3O22S4/c1-13-61(30(6)62)32-25-76-37(23-36(32)71-7)81-50-45(66)42(27(3)78-55(50)80-35-18-16-14-15-17-20-57(70)24-34(64)43(59-56(69)75-11)40(35)31(57)19-21-85-87-84-12)60-83-38-22-33(63)52(29(5)77-38)86-53(68)39-26(2)41(58)48(51(74-10)47(39)72-8)82-54-46(67)49(73-9)44(65)28(4)79-54/h14-15,19,27-29,32-33,35-38,42,44-46,49-50,52,54-55,60,63,65-67,70H,13,21-25H2,1-12H3,(H,59,69)/b15-14-,31-19+/t27-,28+,29-,32+,33+,35+,36+,37+,38+,42-,44+,45+,46-,49-,50-,52-,54+,55+,57+/m1/s1
InChIKey
WPDOZYZAJKUVRZ-IOCYQWGVSA-N
Density
1.6±0.1 g/cm3
Solubility
Soluble in DMSO (10 mm)
Appearance
Solid Powder
Purity
95%
Quantity
Milligrams-Grams
Shelf Life
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Shipping
Room temperature
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Pictograms
Irritant; Acute Toxic; Health Hazard
Signal Word
Danger
1.Gemtuzumab ozogamicin in the treatment of acute myeloid leukemia.
Stasi R;Evangelista ML;Buccisano F;Venditti A;Amadori S Cancer Treat Rev. 2008 Feb;34(1):49-60. Epub 2007 Oct 17.
Gemtuzumab ozogamicin (GO) is a chemotherapeutic agent that consists of a humanized anti-CD33 antibody (hP67.6) linked to N-acetyl-calicheamicin 1,2-dimethyl hydrazine dichloride, a potent enediyne antitumor antibiotic. GO was approved conditionally by the Federal Drug Administration in May 2000 as single-agent therapy for first recurrence of acute myeloid leukemia (AML) in patients over the age of 60 years who are unfit for conventional cytotoxic therapy. In this setting, it produces a complete response (CR) rate of 13%, with another 13% achieving CR with inadequate platelet recovery (CRp). The most common adverse effects associated with GO are infusion-related reactions and myelosuppression. GO monotherapy at the dose of 9 mg/m(2) is complicated with hepatic veno-occlusive disease in approximately 5% of cases, particularly prior to or following stem cell transplantation. Attenuated doses of GO or fractionated doses appear to be equally effective and better tolerated. GO has shown remarkable activity in acute promyelocytic leukemia, particularly for the elimination of minimal residual disease. Combinations of GO with chemotherapy as induction or post-remission therapy are promising, and phase III trials are ongoing.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Historical Records: N-Acetyl-Calicheamicin
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