Demeclocycline

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

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].

Name	demeclocycline
Synonym	More Synonyms

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	Research Areas >> Cancer Research Areas >> Infection Research Areas >> Inflammation/Immunology Signaling Pathways >> Anti-infection >> Bacterial
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
CAS#:14206-59-8 4-Epidemeclocycline

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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China
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China
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China
Product Name: demeclocycline
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Demeclocycline

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