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127-33-3

127-33-3 structure
127-33-3 structure
  • Name: Demeclocycline
  • Chemical Name: demeclocycline
  • CAS Number: 127-33-3
  • Molecular Formula: C21H21ClN2O8
  • Molecular Weight: 464.853
  • Catalog: Signaling Pathways Anti-infection Bacterial
  • Create Date: 2018-08-10 09:05:33
  • Modify Date: 2024-01-05 17:41:57
  • Demeclocycline is an orally active tetracycline antibiotic. Demeclocycline impairs protein synthesis by binding to the 30S ribosomal subunit to inhibit binding of aminoacyl tRNA. Demeclocycline shows anti-bacterial activitise to a wide variety of bacterial infections[1][2].
Name demeclocycline
Synonyms Ledermycin hydrochloride
7-chloro-6-demethyltetracycline
6-demethyl-7-chlorotetracycline
(2E,4S,4aS,5aS,6S,12aS)-2-[Amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
Elkamicina
DMCTC
(4aS)-7-Chlor-4c-dimethylamino-3,6t,10,12,12a-pentahydroxy-1,11-dioxo-(4ar,5ac,12ac)-1,4,4a,5,5a,6,11,12a-octahydro-naphthacen-2-carbonsaeure-amid
Declomycin
EINECS 204-834-8
Demeclocyclinum
7-chloro-4-dimethylamino-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide
(2E,4S,4aS,5aS,6S,12aS)-2-[Amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5a,6,12a-tetrahydro-1,3,12(2H,4H,5H)-tetracenetrione
1,3,12(2H,4H,5H)-Naphthacenetrione, 2-(aminohydroxymethylene)-7-chloro-4-(dimethylamino)-4a,5a,6,12a-tetrahydro-6,10,11,12a-tetrahydroxy-, (2E,4S,4aS,5aS,6S,12aS)-
Demethylchlortetracycline(DMCT)
Demeclociclina
Ledermycin
domeclocycline
(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
Description Demeclocycline is an orally active tetracycline antibiotic. Demeclocycline impairs protein synthesis by binding to the 30S ribosomal subunit to inhibit binding of aminoacyl tRNA. Demeclocycline shows anti-bacterial activitise to a wide variety of bacterial infections[1][2].
Related Catalog
In Vitro Demeclocycline (0-100 μM; 24 h) treatment reduces AQP2 abundance in mpkCCD cells[3]. Demeclocycline (10 μM; 24 h) treatment promotes the activity of monocytes and macrophages[4]. Demeclocycline (1-10 μM; 72 h) treatment directly affects the growth of brain tumorinitiating cells[4]. Western Blot Analysis[3] Cell Line: MpkCCD cells Concentration: 0-100 μM Incubation Time: 24 hours Result: Decreased AQP2 abundance in mpkCCD cells, with significant effects at 50 μM. Cell Viability Assay[4] Cell Line: mouse bone marrow derived macrophages and monocytes Concentration: 10 μM Incubation Time: 24 hours Result: Enhanced TNF-α production and modulated monocyte functions. Cell Viability Assay[4] Cell Line: brain tumorinitiating cells Concentration: 1, 5, and 10 μM Incubation Time: 72 hours Result: Inhibited cells growth in two ways: using monocytes as an intermediary, and directly by affecting the proliferation and sphere-forming capacity of brain tumorinitiating cells.
In Vivo Demeclocycline (Intraperitoneal injection; 40 mg/kg; once daily; 48 h) treatment results in a significant reduction of hyponatremia and a significant correction of the hypoosmolality, and is not nephrotoxic[3]. Animal Model: Male Wistar rats induced with hyponatremia[3] Dosage: 40 mg/kg Administration: Intraperitoneal injection; 40 mg/kg; once daily; 48 hours Result: Increased urine volume, decreased urine osmolality, and caused a significantly increased fractional excretion of water. Animal Model: Male Wistar rats induced with hyponatremia[3] Dosage: 40 mg/kg Administration: Intraperitoneal injection; 40 mg/kg; once daily; 48 hours Result: Indicated the effect in the renal inner medulla for AQP2 and AC5/6 specifically, and not secondary toxicity effect.
References

[1]. I Chopra, et al. Tetracyclines, molecular and clinical aspects. J Antimicrob Chemother. 1992 Mar;29(3):245-77.

[2]. D Schnappinger, et al. Tetracyclines: antibiotic action, uptake, and resistance mechanisms. Arch Microbiol. 1996 Jun;165(6):359-69.

[3]. Marleen L A Kortenoeven, et al. Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla. Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1705-18.

[4]. Susobhan Sarkar, et al. Demeclocycline Reduces the Growth of Human Brain Tumor-Initiating Cells: Direct Activity and Through Monocytes. Front Immunol. 2020 Feb 21;11:272.
Density 1.8±0.1 g/cm3
Boiling Point 684.5±55.0 °C at 760 mmHg
Molecular Formula C21H21ClN2O8
Molecular Weight 464.853
Flash Point 367.8±31.5 °C
Exact Mass 464.098633
PSA 181.62000
LogP 0.57
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.761

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QI7650000
CHEMICAL NAME :
2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octah ydro- 3,6,10,12,12a-pentahydroxy-1,11-dioxo-
CAS REGISTRY NUMBER :
127-33-3
LAST UPDATED :
199706
DATA ITEMS CITED :
15
MOLECULAR FORMULA :
C21-H21-Cl-N2-O8
MOLECULAR WEIGHT :
464.89
WISWESSER LINE NOTATION :
L E6 C666 BV FV CU GUTTT&J DQ EQ GVZ HQ IN1&1 MQ OG RQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
420 mg/kg/6W
TOXIC EFFECTS :
Endocrine - diabetes insipidus (nephrogenic or CNS) Biochemical - Metabolism (Intermediary) - effect on cyclic nucleotides
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
10 mg/kg
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
68 mg/kg/8D
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - other changes in urine composition
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>6750 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
358 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
454 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
79 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
240 mg/kg
SEX/DURATION :
female 1-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other postnatal measures or effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5 gm/kg
SEX/DURATION :
female 1-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5 gm/kg
SEX/DURATION :
female 1-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other postnatal measures or effects

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
3750 ug/L
REFERENCE :
BCPHBM British Journal of Clinical Pharmacology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1974- Volume(issue)/page/year: 16,127,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5539 No. of Facilities: 10 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 330 (estimated) No. of Female Employees: 120 (estimated)
Precursor  0

DownStream  1


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