CAS 389-08-2 MFCD00006884-Nalidixic Acid 萘啶酮酸 TAO{mole}

Nalidixic Acid 萘啶酮酸

CAS 389-08-2 MFCD00006884

化学结构图

SMILES: CCn1cc(C(=O)O)c(=O)c2ccc(C)nc21

化学属性

Mol. Formula	C12
Mol. Weight	232
Melting Point	227.0 to 231.0 deg-C
TSCA	No
Solubility	0.1 G/L (23 ºC)
Appearance	本品为浅黄色结晶粉末。溶于氯仿，微溶于醇、强碱液，几乎不溶于水和醚。
Density	1.331

别名和识别编码

Chemical Name	Nalidixic Acid
Synonym	1,4-DIHYDRO-1-ETHYL-7-METHYL-1,8-NAPHTHYRIDIN-4-ONE-3-CARBOXYLIC ACID 1,4-二氢-1-乙基-7-甲基-1,8-萘啶-4-酮-3-羧酸 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxilic acid 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid,1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid 1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylicacid 1-乙基-1,4-二氢-7-甲基-4-氧代-1,8-萘啶-3-羧酸 1-乙基-7-甲基-1,8-萘啶-4-酮-3-羧酸 Acid, Nalidixic Anhydrous, Nalidixate Sodium NOGRAM NSC-82174 Nalidixan Nalidixate Sodium Nalidixate Sodium Anhydrous Nalidixic Acid Nalidixin Nalitucsan Nevigramon Nogram Sodium Anhydrous, Nalidixate Sodium Nalidixic Acid, Anhydrous Sodium Nalidixic Acid, Monohydrate Sodium, Nalid
MDL Number	MFCD00006884
PubChem Substance ID	4421
Beilstein Registry Number	750515
CAS Number	389-08-2
EC Number	206-864-7
Reaxys-RN	750515
Merck Number	6359
Alfabeta Name	ETHYLMETHYLOXODIHYDRONAPHTHYRIDINECARBOXYLICACID 17414183-----------,,
Chemical Name Translation	萘啶酮酸
Wiswesser Line Notation	T66 BN EV JNJ B2 DVQ I1
LabNetwork Molecule ID	LN00179330
InChI	InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

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产品应用

细菌DNA合成酶(DNA gyrase) 和鸟类成骨髓细胞瘤病毒反转录酶（avian myeloblastoma virus reverse transcriptase）的抑制剂。

安全信息

WGK Germany2

GHS Symbol

Precautionary statements

P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
P285 In case of inadequate ventilation wear respiratory protection. 在通风不足的情况下，戴呼吸防护。
P301+P312
P302+P352
P304+P341
P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
P330 Rinse mouth. 漱口
P333+P313
P342+P311
P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
P501 Dispose of contents/container to..… 处理内容物/容器.....

Hazard statements

H302 Harmful if swallowed 吞食有害
H303 May be harmfully swallowed 吞食可能有害
H317 May cause an allergic skin reaction 可能导致皮肤过敏
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled 吸入可能导致过敏或哮喘症状或呼吸困难

RTECSQN2885000

Personal Protective Equipment Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Signal word

Safety Statements

Risk Statements

R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
R42/43
R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
R22 Harmful if swallowed 吞咽有害

Hazard Codes Xn

Warnings IRRITANT

Storage condition 室温保存 0-6°C

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 173 gm/kg/2Y-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Skin and Appendages - tumors
REFERENCE :
   NTPTR* National Toxicology Program Technical Report Series.  (Research
   Triangle Park, NC 27709) No.206-  Volume(issue)/page/year: NTP-TR-368,1989

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 173 gm/kg/2Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Skin and Appendages - tumors
   Reproductive - Tumorigenic effects - other reproductive system tumors
REFERENCE :
   NTPTR* National Toxicology Program Technical Report Series.  (Research
   Triangle Park, NC 27709) No.206-  Volume(issue)/page/year: NTP-TR-368,1989

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 160 mg/kg/2D
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Endocrine - hyperglycemia
   Skin and Appendages - sweating
REFERENCE :
   BMJOAE British Medical Journal.  (British Medical Assoc., BMA House,
   Tavistock Sq., London WC1H 9JR, UK)  V.1-    1857- Volume(issue)/page/year:
   2,1518,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED

{haz

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 319 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AACHAX Antimicrobial Agents and Chemotherapy (1961-70).  (Ann Arbor, MI)
   1961-70.  For publisher information, see AMACCQ.  Volume(issue)/page/year:
   -,117,1970

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 572 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   18,185,1971

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 600 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   USXXAM United States Patent Document.  (U.S. Patent Office, Box 9,
   Washington, DC 20231)  Volume(issue)/page/year: #4552882

TYPE OF TEST            : Sex chromosome loss and nondisjunction
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 20 mg/3D
REFERENCE :
   SOGEBZ Soviet Genetics.  English translation of GNKAA5.  (Plenum Pub. Corp.,
   233 Spring St., New York, NY 10013)  V.2-    1966- Volume(issue)/page/year:
   10,128,1974

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 100 mg/L
REFERENCE :
   JOBAAY Journal of Bacteriology.  (American Soc. for Microbiology, 1913 I
   St., NW, Washington, DC 20006)  V.1-    1916-  Volume(issue)/page/year:
   116,1398,1973

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 200 mg/L
REFERENCE :
   MGGEAE Molecular and General Genetics.  (Springer-Verlag, Heidelberger Pl.
   3, D-1000 Berlin 33, Fed. Rep. Ger.)  V.99-

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Bacteria - Serratia marcescens
DOSE/DURATION           : 2200 ug/L
REFERENCE :
   AMACCQ Antimicrobial Agents and Chemotherapy.  (American Soc. for
   Microbiology, 1913 I St., NW, Washington, DC 20006)  V.1-    1972-
   Volume(issue)/page/year: 17,763,1980

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 5 mg/L
REFERENCE :
   VIRLAX Virology.  (Academic Press, Inc., 1 E. First St., Duluth, MN 55802)
   V.1-    1955-  Volume(issue)/page/year: 41,244,1970

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Protozoa - Euglena gracilis
DOSE/DURATION           : 50 mg/L
REFERENCE :
   ABBIA4 Archives of Biochemistry and Biophysics.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802)  V.31-    1951-  Volume(issue)/page/year:

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 3960 mg/kg
SEX/DURATION            : female 7-12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   NKRZAZ Chemotherapy (Tokyo).  (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki,
   Shinagawa-Ku, Tokyo 141, Japan)  V.1-    1953- Volume(issue)/page/year:
   19,422,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1320 mg/kg
SEX/DURATION            : female 9-14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   NKRZAZ Chemotherapy (Tokyo).  (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki,
   Shinagawa-Ku, Tokyo 141, Japan)  V.1-    1953- Volume(issue)/page/year:
   19,422,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 3300 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured
   before birth)
   Reproductive - Effects on Embryo or Fetus - extra-embryonic structures
   (e.g., placenta, umbilical cord)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   NKRZAZ Chemotherapy (Tokyo).  (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki,
   Shinagawa-Ku, Tokyo 141, Japan)  V.1-    1953- Volume(issue)/page/year:
   28(Suppl 4),484,1980

TYPE OF TEST            : TDLo - Lowest published

其他信息

方法一:由2-甲基吡啶制得2-氨基-5-甲基吡啶，再与原甲酸乙酯及丙二酸二乙酯缩合成N-（2-甲基-5-氨基吡啶）甲叉丙二酸二乙酯，然后将其在260-270℃环合后再加入氢氧化钠稀溶液中水解，得到7-甲基-1,8-萘啶-4-羟基-3-羟酸。最后用溴乙烷进行N-烷基化并异构成萘啶酮酸。
图谱信息:萘啶酸(389-08-2)质谱(MS) 萘啶酸(389-08-2)核磁图( 1 HNMR) 萘啶酸(389-08-2)核磁图( 13 CNMR) 萘啶酸(389-08-2)红外图谱(IR1) 萘啶酸(389-08-2)红外图谱(IR2)
用途一:抗感染药，对大肠杆菌、变形杆菌属等杆菌科细菌有一定的抗菌作用
TCI Shanghai:萘啶酸 Nalidixic Acid,>;95.0%(T)(389-08-2)
Alfa Aesar:萘啶酮酸,99% Nalidixic acid, 99%(389-08-2)
用途三:细菌DNA合成酶(DNA gyrase) 和鸟类成骨髓细胞瘤病毒反转录酶（avian myeloblastoma virus reverse transcriptase）的抑制剂。
Acros Organics:萘啶酸 Nalidixic acid, 99.50%(389-08-2)
无气味。几乎无味。对光和空气敏感。23℃时溶解度(mg/mL)：氯仿35，甲苯1.6，甲醇1.3，乙醇0.9，水0.1，乙醚0.1。20℃时溶于350份丙酮，微溶于氢氧化碱溶液。半数致死量(小鼠，经口)3300mg/kg。
MOL 文件:389-08-2.mol
上游原料:原甲酸三乙酯 --> 溴乙烷 --> 丙二酸 --> 3-氨基-6-甲基吡啶 --> 2-氨基-5-甲基吡啶 --> 乙氧基甲叉丙二酸二乙酯 --> 二乙酯 --> 1,8-萘啶
MSDS 信息:1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid(389-08-2).msds
Sigma Aldrich:389-08-2(sigmaaldrich)
用途二:该品为抗菌剂，能抑制细菌DNA、RNA的合成，用于治疗革兰氏阴性细菌所致的尿道感染。萘啶酮酸是喹诺酮类的第一代抗菌药代表，第二代则以吡哌为代表。第三代喹诺酮类抗菌药物的代表是氟哌酸。
萘啶酸价格(试剂级):更新日期产品编号产品名称包装价格 2011/08/23 k7016201 萘啶酮酸 5g 248元 2011/08/23 SN887801 萘啶酮酸 5g 255元 2011/04/16 N0490 萘啶酸 Nalidixic Acid 25G 727元
F:8-10-23