CAS No.23214-92-8,Adriamycin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	23214-92-8
Name:	Adriamycin
Article Data:	89

Formula:	C₂₇H₂₉NO₁₁
Molecular Weight:	543.527
Synonyms:	5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,(8S,10S)- (9CI);14-Hydroxydaunomycin;63: PN: WO2010011890 PAGE: 37 claimedsequence;Biotransdox;Caelyx;Doxil;Doxorubicin;Evacet;Hydroxydaunomycin;NSC 123127;PK 2;Rubex;
EINECS:	245-495-6
Density:	1.615 g/cm³
Melting Point:	205 °C
Boiling Point:	810.293 °C at 760 mmHg
Flash Point:	443.849 °C
Solubility:	soluble in water
Appearance:	orange to red powder
PSA:	206.07000
LogP:	1.50360

Raw Materials

Downstream Products

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Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 82.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 82.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 82.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .

Specification

The IUPAC name of Adriamycin is (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione. With the CAS registry number 23214-92-8 and EINECS 245-495-6, it is also named as Doxorubicin. The classification codes are Antibiotics, Antineoplastic; Antineoplastic; Antineoplastic agents; Drug / Therapeutic Agent; Human Data; Mutation data; Natural Product; Reproductive Effect; Skin / Eye Irritant; Tumor data. It is highly toxic and flammable. When heated to decomposition it emits very toxic fumes of NO_x and HCl. So the storage environment should be well-ventilated, low-temperature and dry. Keep Adriamycin separate from raw materials of food. What's more, this drug is photosensitive, and containers are often covered by an aluminum bag and/or brown wax paper to prevent light from affecting it.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.24; (2)# of Rule of 5 Violations: 3; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 12; (8)#H bond donors: 7; (9)#Freely Rotating Bonds: 11; (10)Polar Surface Area: 206.07 Å²; (11)Index of Refraction: 1.71; (12)Molar Refractivity: 131.521 cm³; (13)Molar Volume: 336.639 cm³; (14)Surface Tension: 96.438 dyne/cm; (15)Enthalpy of Vaporization: 123.508 kJ/mol; (16)Vapour Pressure: 0 mmHg at 25°C; (17)Rotatable Bond Count: 5; (18)Tautomer Count: 81; (19)Exact Mass: 543.174061; (20)MonoIsotopic Mass: 543.174061; (21)Topological Polar Surface Area: 206; (22)Heavy Atom Count: 39; (23)Complexity: 977.

Preparation and Uses of Adriamycin: Antineoplastic antibiotic obtained from Streptomyces peucetius. It is used in the treatment of a wide range of cancers, including hematological malignancies, many types of carcinoma, and soft tissue sarcomas. The most serious adverse effect of this drug is life-threatening heart damage. In addition, this chemical can react with formaldehyde to get doxoform. This reaction needs reagent Et₃N*AcOH and AcOH at temperature of 25 °C. The reaction time is 15 hours. The yield is 70%.

People can use the following data to convert to the molecule structure.
1. SMILES:C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)CO)O)N)O
2. InChI:InChI=1/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
3. InChIKey:AOJJSUZBOXZQNB-TZSSRYMLBG

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	2400ug/kg (2.4mg/kg)		Drug and Chemical Toxicology. Vol. 6, Pg. 21, 1983.
hamster	LD10	parenteral	3500ug/kg (3.5mg/kg)		Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
human	LDLo	intravenous	400ug/kg (0.4mg/kg)	GASTROINTESTINAL: OTHER CHANGES BLOOD: LEUKOPENIA SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Cancer Chemotherapy Reports, Part 3. Vol. 3, Pg. 33, 1972.
human	TDLo	intravenous	15mg/kg/D (15mg/kg)	CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Cancer Vol. 34, Pg. 518, 1974.
human	TDLo	intravenous	380mg/kg/31W (380mg/kg)	CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Cancer Vol. 34, Pg. 518, 1974.
mammal (species unspecified)	LD50	intraperitoneal	8500ug/kg (8.5mg/kg)		Antibiotiki. Vol. 29, Pg. 748, 1984.
man	LDLo	unreported	243ug/kg (0.243mg/kg)	CARDIAC: OTHER CHANGES VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Postgraduate Medical Journal. Vol. 68, Pg. 69, 1992.
mouse	LD50	intraperitoneal	10700ug/kg (10.7mg/kg)		Huaxi Yike Daxue Xuebao. Journal of West China University of Medical Sciences. Vol. 20, Pg. 303, 1989.
mouse	LD50	intravenous	10mg/kg (10mg/kg)		Journal of Antibiotics. Vol. 45, Pg. 1373, 1992.
mouse	LD50	oral	570mg/kg (570mg/kg)		Antibiotiki. Vol. 28, Pg. 298, 1983.
mouse	LD50	unreported	21900ug/kg (21.9mg/kg)		Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.
mouse	LDLo	intratracheal	2400ug/kg (2.4mg/kg)		Toxicology Letters. Vol. 30, Pg. 63, 1986.
rabbit	LD50	intravenous	5mg/kg (5mg/kg)		Yiyao Gongye. Pharmaceutical Industry. Vol. 17, Pg. 72, 1986.
rabbit	LDLo	intrapleural	400ug/kg (0.4mg/kg)	CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: PLEURAL THICKENING LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"	Pharmacology and Toxicology Vol. 62, Pg. 84, 1988.
rat	LD50	intraperitoneal	16mg/kg (16mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1075, 1972.
rat	LD50	intravenous	10510ug/kg (10.51mg/kg)		Toxicology and Applied Pharmacology. Vol. 79, Pg. 412, 1985.
rat	LD50	unreported	7mg/kg (7mg/kg)		Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 34, Pg. 216, 1989.