Gemcitabine HCl

Modify Date: 2024-01-02 19:08:34

Gemcitabine HCl Structure
Gemcitabine HCl structure
 Common Name Gemcitabine HCl
CAS Number 122111-03-9 Molecular Weight 299.659
Density N/A Boiling Point 482.7ºC at 760 mmHg
Molecular Formula C9H12ClF2N3O4 Melting Point >250°C dec.
MSDS Chinese USA Flash Point N/A
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Gemcitabine HCl


Gemcitabine hydrochloride is a DNA synthesis inhibitor with IC50s of 37.6, 42.9, 92.7, 89.3 and 131.4 nM in BxPC-3, Mia Paca-2, PANC-1, PL-45 and AsPC-1 cells, respectively.

 Names

Name gemcitabine hydrochloride
Synonym More Synonyms

 Gemcitabine HCl Biological Activity

Description Gemcitabine hydrochloride is a DNA synthesis inhibitor with IC50s of 37.6, 42.9, 92.7, 89.3 and 131.4 nM in BxPC-3, Mia Paca-2, PANC-1, PL-45 and AsPC-1 cells, respectively.
Related Catalog
Target

DNA synthesis[1]

In Vitro MTS assay demonstrates that Gemcitabine at 15 nM, indole-3-carbinol (I3C) at 50 μM and the combination does not affect hTERT-HPNE cell viability. However, treatment with Gemcitabine at 15 nM, I3C at 50 μM and the combination results in 31%, 19% and 72% cell death of BxPC-3 cells, respectively[1].
In Vivo The aim of study is to formulate PLGA nanoparticles (NPs) of Gemcitabine Hydrochloride (Gemcitabine HCl) for enhanced oral bioavailability via absorption through M cells of Peyer’s patches. Gemcitabine HCl is available as i.v. infusion due to its short half life (8-17 min), rapid metabolism and limited tumor uptake. Gemcitabine loaded PLGA NPs shows 21.47-fold increase in relative bioavailability in comparison to plain drug solution after oral delivery[2]. After i.v. injection of Gemcitabine at doses of 50, 100, and 120, and 300 mg/kg, the highest dose caused considerable body weight loss (p<0.05 at all the time points evaluated, starting from day 3 of first injection) compared with that of the untreated group and complete mortality, whereas 120 mg/kg is determined as the lethal dose 10% (LD10) and 100 mg/kg is considered as the maximal tolerated dose, which does not cause any mortality and a minimal body weight loss[3].
Cell Assay Cells (the human pancreatic cell lines, Mia PaCa-2, BxPC-3, AsPC-1, PANC-1, PL-45, and normal pancreatic ductal epithelial cells, hTERT-HPNE cells) are seeded into 96-well plates (3000 cells/well) in triplicate. After overnight incubation, the medium is changed and cells are treated with I3C and/or NBMPR for 24 h. The medium is changed again and cells are cultured in medium containing different concentrations of Gemcitabine in the presence or absence of the same concentrations of I3C and/or NBMPR for 48 h. The cells are then subjected to CellTiter 96 AQueous One Solution Cell Proliferation Assay (MTS). Absorbance at 490 nm is measured 2 h after the addition of 20 μL of MTS reagent/well[1]. The in vitro cytotoxicity of Gemcitabine HCl loaded NPs on Caco-2 cells are performed for 6 h to check the toxicity of NPs during the transport/permeability studies and antiproliferative effect on K562 cells is evaluated for 48 h using the MTT assay. The cells are cultured in 96-well plates at a seeding density of 1.0×104 cells/well for 48 h. Experiments are initiated by replacing the culture medium in each well with 150 μL of sample solutions (0.1, 1, 10, 100 μg/mL) at 37°C in the CO2 incubator. After 4, 24 and 48 h of incubation, the medium is removed and 150 μL of MTT reagent (1 mg/mL) in the serum-free medium is added to each well. The plates are then incubated at 37°C for another 4 h. At the end of the incubation period, the medium is removed and the intracellular formazan is solubilized with 150 μL DMSO and quantified by reading the absorbance at 590 nm on a micro-plate multi-detection instrument, SpectraMax M2 with Soft Max Pro. The medium treated cells serve as controls. Percentage cell viability is calculated based on the absorbance measured relative to the absorbance of cells exposed to the negative control[2].
Animal Admin Rats[2] Three groups of male Wistar rats (n=6) are subjected to single oral dose bioavailability study. The formulations are administered orally with the aid of a syringe and infant feeding tube. The 1st group is given distilled water, the 2nd group is given a solution of Gemcitabine HCl in distilled water, and the third group received Gemcitabine HCl loaded NPs at a dose of 10 mg/kg. Blood samples (0.3 mL) are drawn by retro-orbital venous plexus puncture with the aid of capillary tubes at 0.5, 1, 2, 4, 24, 48, 72 h post oral dose. The samples are collected in heparinised Eppendorf tubes containing 10 μM tetrahydrouridine, centrifuged at 3400 rpm for 15 min and plasma is collected. To this, 200 μL of Acetonitrile is added and vortexed for 5 min followed by centrifugation at 5000 rpm for 15 min. The organic phase is separated and evaporated under reduced pressure in a vacuum oven. The residue is dissolved in mobile phase (0.15 mL), vortexed for 1 min followed by centrifugation at 13,000 rpm for 5 min. Then 20 μL of supernatant is injected into the HPLC column and analyzed by HPLC. Mice[3] DBA/2 mice (5-6 weeks old), weighing approximately 15 to 18 g, are used for the study. The mice are provided with standard mouse food and water ad libitum. The L1210 wt leukemia cells are maintained in vitro, and they are injected intravenously (1×105) into the mice, to develop a systemic metastatic leukemia model. The mice are divided into six groups of seven to eight mice each: untreated, treated with squalene nanoparticles, treated with 100 mg/kg Gemcitabine, treated with 20 mg/kg equivalent SQgem nanoassemblies in Gemcitabine, treated with 100 mg/kg cytarabine, and treated with 100 mg/kg cytarabine every day for 5 days. After injection of leukemia cells (day 0), all groups of mice received the treatment by i.v. injection on days 1, 5, 9, and 14 (i.e., days after injecting leukemia cells), with the exception of the untreated group and the group treated with cytarabine daily by the i.v. route. The mice are monitored regularly for weight differences and survival.
References

[1]. Wang H, et al. Enhanced efficacy of Gemcitabine by indole-3-carbinol in pancreatic cell lines: the role of human equilibrativenucleoside transporter 1. Anticancer Res. 2011 Oct;31(10):3171-80

[2]. Joshi G, et al. Enhanced bioavailability and intestinal uptake of Gemcitabine HCl loaded PLGA nanoparticles after oral delivery. Eur J Pharm Sci. 2014 Aug 18;60:80-9.

[3]. Reddy LH, et al. Preclinical toxicology (subacute and acute) and efficacy of a new squalenoyl Gemcitabine anticancernanomedicine. J Pharmacol Exp Ther. 2008 May;325(2):484-90.

 Chemical & Physical Properties

Boiling Point 482.7ºC at 760 mmHg
Melting Point >250°C dec.
Molecular Formula C9H12ClF2N3O4
Molecular Weight 299.659
Exact Mass 299.048431
PSA 110.60000
LogP 0.09460
Vapour Pressure 2.41E-11mmHg at 25°C
Storage condition Desiccate at +4°C

 MSDS

Section I.Chemical Product and Company Identification
Chemical Name Gemcitabine Hydrochloride
Portland OR
SynonymCytidine, 2'-deoxy-2',2'-difluoro-, hydrochloride (1:1)
(CA INDEX NAME)
Chemical FormulaC9H11F2N3O4 · HCl
CAS Number122111-03-9
Section II.Composition and Information on Ingredients
Toxicology Data
Chemical NameCAS Number Percent (%)TLV/PEL
Min. 98.0 Not available.Rat LD50 (intravenous) 236 mg/kg
Gemcitabine Hydrochloride122111-03-9
(HPLC,N)Mouse LD50 (intravenous) 500
mg/kg
Section III. Hazards Identification
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
Acute Health Effects
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive effects.
Mouse TDLo Intravenous 15 mg/kg, female 6-15 days of pregnancy
Toxic Effects:
Maternal Effects - Parturition
Effects on Fertility - Post-implantation mortality
Effects on Fertility - Litter size
Mouse TDLo Intravenous 15 mg/kg, female 6-15 days of pregnancy
Toxic Effects:
Maternal Effects - Other effects
Effects on Embryo or Fetus - Fetotoxicity
Effects on Embryo or Fetus - Fetal death
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Section IV.First Aid Measures
Eye ContactCheck for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin ContactIn case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Ingestion
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.
Section V.Fire and Explosion Data
Not available.
May be combustible at high temperature.Auto-Ignition
Flammability
Flash PointsFlammable LimitsNot available.
Not available.
These products are toxic carbon oxides (CO, CO2), nitrogen oxides (NO, NO2), halogenated compounds.
Combustion Products
WARNING: Highly toxic HCl gas is produced during combustion.
WARNING: Highly toxic HF gas is produced during combustion.
Fire Hazards
Not available.
Continued on Next Page
Gemcitabine Hydrochloride
Explosion HazardsRisks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting MediaSMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Section VI.Accidental Release Measures
Spill CleanupIrritating material. This material is a reproductive effector.
Use a shovel to put the material into a convenient waste disposal container. Consult federal, state, and/or local authorities for
Instructions
assistance on disposal.
Section VII. Handling and Storage
IRRITANT. REPRODUCTIVE EFFECTOR. Keep away from heat. Mechanical exhaust required. When not in use, tightly
Handling and Storage
seal the container and store in a dry, cool place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents.
Section VIII. Exposure Controls/Personal Protection
Engineering ControlsUse process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Personal ProtectionSplash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Not available.
Exposure Limits
Section IX. Physical and Chemical Properties
Physical state @ 20°CSolid. (White crystalline powder.)SolubilitySoluble in hot water.
Not available.
Specific Gravity
Molecular Weight299.66Partition CoefficientNot available.
Boiling PointNot available.Not applicable.
Vapor Pressure
Melting Point287 to 292°C (548.6 to 557.6°F) (dec.)Vapor DensityNot available.
Not available.Not available.
Refractive IndexVolatility
Critical TemperatureNot available.OdorNot available.
Not available.Not available.
ViscosityTaste
Section X.Stability and Reactivity Data
This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of InstabilityAvoid excessive heat and light.
IncompatibilitiesReactive with oxidizing agents.
Section XI. Toxicological Information
RTECS NumberHA3840000
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Rat LD50 (intravenous) 236 mg/kg
Toxicity Data
Mouse LD50 (intravenous) 500 mg/kg
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive effects.
Mouse TDLo Intravenous 15 mg/kg, female 6-15 days of pregnancy
Toxic Effects:
Maternal Effects - Parturition
Effects on Fertility - Post-implantation mortality
Effects on Fertility - Litter size
Mouse TDLo Intravenous 15 mg/kg, female 6-15 days of pregnancy
Toxic Effects:
Maternal Effects - Other effects
Effects on Embryo or Fetus - Fetotoxicity
Effects on Embryo or Fetus - Fetal death
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Continued on Next Page
Gemcitabine Hydrochloride
Acute Toxic EffectsIrritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Section XII.Ecological Information
Not available.
Ecotoxicity
Environmental FateNot available.
Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.
Section XIV. Transport Information
DOT ClassificationNot a DOT controlled material (United States).
PIN NumberNot applicable.
Proper Shipping NameNot applicable.
Packing Group (PG)Not applicable.
DOT Pictograms
Section XV. Other Regulatory Information and Pictograms
TSCA Chemical InventoryThis product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS ClassificationNot available.
(Canada)
EINECS Number (EEC) 601-823-3
EEC Risk StatementsR36/37/38- Irritating to eyes, respiratory system and skin.
R60- May impair fertility.
R61- May cause harm to the unborn child.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HA3840000
CHEMICAL NAME :
Cytidine, 2'-deoxy-2',2'-difluoro-, monohydrochloride
CAS REGISTRY NUMBER :
122111-03-9
LAST UPDATED :
199706
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C9-H11-F2-N3-O4.Cl-H
MOLECULAR WEIGHT :
299.69

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
15 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 48,365,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
15 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 48,365,1993

 Safety Information

Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H360
Precautionary Statements P201-P280-P308 + P313
Hazard Codes Xi: Irritant;
Risk Phrases R21
Safety Phrases 25-26-36/37-53
RIDADR NONH for all modes of transport
HS Code 2934999090

 Synthetic Route

Gemcitabine structure

Gemcitabine

CAS#:95058-81-4

~89%

Gemcitabine HCl Structure

Gemcitabine HCl

CAS#:122111-03-9

Literature: Hanmi Pharm. Co.,Ltd Patent: US2007/249818 A1, 2007 ; Location in patent: Page/Page column 10 ;
2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-di benzoate structure

2-Deoxy-2,2-dif...

CAS#:1173824-58-2

N-trimethylsilyl-N-(2-trimethylsilyloxypyrimidin-4-yl)acetamide structure

N-trimethylsily...

CAS#:18027-23-1

~51%

Gemcitabine HCl Structure

Gemcitabine HCl

CAS#:122111-03-9

Literature: KANNAN, Vishwanath; KASH, Vishwanathan Patent: WO2010/29574 A2, 2010 ; Location in patent: Page/Page column 8-9 ;
gemcitabine structure

gemcitabine

CAS#:103882-84-4

~%

4-Amino-1-(2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone Hydrochloride structure

4-Amino-1-(2-de...

CAS#:122111-05-1

Gemcitabine HCl Structure

Gemcitabine HCl

CAS#:122111-03-9

Literature: WO2007/117760 A2, ; Page/Page column 21 ;
N-Acetyl cytosine structure

N-Acetyl cytosine

CAS#:14631-20-0

2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate structure

2-Deoxy-2,2-dif...

CAS#:134877-42-2

~%

4-Amino-1-(2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone Hydrochloride structure

4-Amino-1-(2-de...

CAS#:122111-05-1

Gemcitabine HCl Structure

Gemcitabine HCl

CAS#:122111-03-9

Literature: WO2005/95430 A1, ; Page/Page column 18-20 ;
gemcitabine structure

gemcitabine

CAS#:103882-84-4

~%

Gemcitabine HCl Structure

Gemcitabine HCl

CAS#:122111-03-9

Literature: WO2007/49294 A1, ; Page/Page column 10-11 ;
α/β-1-(2-oxo-4-amino-1H-pyrimidin-1-yl)-2-desoxy-2,2'-difluororibose hydrochloride structure

α/β-1-(2-oxo-4-...

CAS#:951314-37-7

~%

Gemcitabine HCl Structure

Gemcitabine HCl

CAS#:122111-03-9

Literature: WO2007/112473 A1, ; Page/Page column 8-9 ;

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

dFdC,Gemzar,Lilly)
MFCD01735988
dFdC Gemzar (Lilly) LY-188011 dFdC dFdCyd
4-Amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one hydrochloride
Gemcitabine hydrochloride
2'-Deoxy-2',2'-difluorocytidine
4-Amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone hydrochloride
Cytidine, 2'-deoxy-2',2'-difluoro-, hydrochloride (1:1)
2'-Deoxy-2',2'-difluorocytidine hydrochloride (1:1)
Gemcitabine HCl
Gemcitabine HCl(TABINES)
Gemcitabine (Hydrochloride)
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