midecamycin

Names

[ Name ]:
midecamycin

[Synonym ]:
(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-4-(Dimethylamino)-3-hydroxy-5-{[(2S,4R,5S,6S)-4-hydroxy-4,6-dimethyl-5-(propionyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-methyltetrahydro-2H-pyran-2-yl]oxy}-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-4-yl propanoate
MFCD00070321
Antibiotic SF 837
YL 704B1
Mydecamycin
(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-4-(Dimethylamino)-3-hydroxy-5-{[(2S,4R,5S,6S)-4-hydroxy-4,6-dimethyl-5-(propionyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-methyltetrahydro-2H-pyran-2-yl]oxy}-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-4-yl propanoate (non-preferred name)
Macro-Dil
Macropen
Espinomycin A
Medemycin
Turimycin P3
Antibiotic YL 704B1
Madecacine
midecamycin
EINECS 252-578-0
Leucomycin V 3,4B-Dipropanoate
Platenomycin B1

Biological Activity

[Description]:

Midecamycin, an acetoxy-substituted macrolide antibiotic, is tested against gram-positive and gram-negative bacteria.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Natural Products >> Others

Research Areas >> Infection

[Target]

Antibacterial[1]

[In Vitro]

Midecamycin inhibits the majority of streptococci, staphylococci, and strains of Haemophilus and Listeria at concentrations of less than 3.1 μg/mL[1]. Midecamycin is a 16-membered macrolide. Midecamycin is a new macrolide antibiotic, which is produced by Streptomyces mycarofaciens[2].

[References]

[1]. Neu HC. In vitro activity of midecamycin, a new macrolide antibiotic. Antimicrob Agents Chemother. 1983 Sep;24(3):443-4.

[2]. Cong L, et al. Cloning and characterization of genes encoded in dTDP-D-mycaminose biosynthetic pathway from amidecamycin-producing strain, Streptomyces mycarofaciens. Acta Biochim Biophys Sin (Shanghai). 2007 Mar;39(3):187-93.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
874.0±65.0 °C at 760 mmHg

[ Melting Point ]:
155℃ -156℃

[ Molecular Formula ]:
C₄₁H₆₇NO₁₅

[ Molecular Weight ]:
813.968

[ Flash Point ]:
482.4±34.3 °C

[ Exact Mass ]:
813.451050

[ PSA ]:
206.05000

[ LogP ]:
3.53

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OH4730600

CHEMICAL NAME :: Leucomycin V, 3,4(sup B)-dipropanoate

CAS REGISTRY NUMBER :: 35457-80-8

LAST UPDATED :: 199806

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C41-H67-N-O15

MOLECULAR WEIGHT :: 814.09

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,810,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 11300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1330,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1330,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,810,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 910 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 21,711,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 21,711,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 2,83,1980 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 18 gm/kg

SEX/DURATION :: female 10-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 25,187,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: female 10-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 25,187,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 gm/kg

SEX/DURATION :: female 10-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 25,187,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: female 8-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 25,193,1972

Safety Information

[ RTECS ]:
OH4730600

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.