Demeclocycline

Modify Date: 2024-01-05 17:41:57

Demeclocycline Structure
Demeclocycline structure
 Common Name Demeclocycline
CAS Number 127-33-3 Molecular Weight 464.853
Density 1.8±0.1 g/cm3 Boiling Point 684.5±55.0 °C at 760 mmHg
Molecular Formula C21H21ClN2O8 Melting Point N/A
MSDS N/A Flash Point 367.8±31.5 °C

 Use of Demeclocycline


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].

 Names

Name demeclocycline
Synonym More Synonyms

 Demeclocycline Biological Activity

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.

 Chemical & Physical Properties

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

 Toxicological Information

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 & DownStream

Precursor  0

DownStream  1

 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
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Related Compounds: More...
demeclocycline
106276-91-9
4-Epidemeclocycline
14206-59-8
Demeclocycline calcium
17146-81-5
Demeclocycline hydrochloride
64-73-3
Des(dimethylamino)-4-hydrazone Demeclocycline
1177-81-7
Chemsrc provides Demeclocycline(CAS#:127-33-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Demeclocycline are included as well.>> amp version: Demeclocycline

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